Back to results
US 2003/0204100 A1Published application
Process for preparation of a benzofuran derivative
AssigneeChugai Seiyaku Kabushiki Kaisha
InventorsKunio Tamura, Hirohito Shimizu, Yoshiaki Kato, Masahiro Shimizu
Life of this patent
Estimating the term…
Abstract
An industrially useful process for producing benzofuran derivatives of formula (1) 1 by formylating a compound of formula (2) 2 (where A1 is a protective group), followed by reaction with a compound of formula (4) 3 (where X1 is a halogen atom), then performing a cyclizing reaction and subsequently performing a reaction for hydroxyl group deprotection.
Claims17
A process for producing a compound represented by formula (1)
- 56
- which comprises the first step of formylating a compound represented by formula (2)
- 57
- (where A1 is a protective group) to give a compound represented by formula (3)
- 58
- (where A1 is a protective group), the third step of reacting the compound of formula (3) with a metal hydride and thereafter reacting the same with a compound represented by formula (4)
- 59
- (where X1 is a halogen atom) to give a compound represented by formula (5)
- 60
- (where A1 is a protective group), the fifth step of cyclizing the compound of formula (5) to give a compound represented by formula (6)
- 61
- (where A1 is a protective group), and the seventh step of deprotecting the compound of formula (6) to give a compound represented by formula (1)
- 62
10 more elements
A process for producing a compound represented by formula (1)
- 63
- which comprises the first step of formulating a compound represented by formula (2)
- 64
- (where A1 is a protective group) to give a compound represented by formula (3)
- 65
- (where A1 is a protective group), the second step of recrystallizing the compound of formula (3) in a lower alcohol/water mixed solvent to give a purified form of the compound of formula (3), the third step of reacting the compound of formula (3) with a metal hydride and thereafter reacting the same with a compound represented by formula (4)
- 66
- (where X1 is a halogen atom) to give a compound represented by formula (5)
- 67
- (where A1 is a protective group), the fourth step of recrystallizing the compound of formula (5) in a hydrocarbon or in a lower alcohol/water mixed solvent to give a purified form of the compound of formula (5), the fifth step of cyclizing the compound of formula (5) to give a compound represented by formula (6)
- 68
- (where A1 is a protective group), the sixth step of treating the compound of formula (6) with an alkali in a lower alcohol and thereafter treating the same with aluminum oxide to give a purified form of the compound of formula (6), and the seventh step of deprotecting the compound of formula (6) to give a compound represented by formula (1)
- 69
10 more elements
A process comprising the fifteenth step of treating a compound of formula (12)
- 79
- (where X2 is a halogen atom) with magnesium in diethyl ether or tetrahydrofuran to give a compound represented by formula (13)
- 80
- (where X2 is a halogen atom) and treating the obtained compound with a formic acid ester to give a compound represented by formula (14)
- 81
- treating the obtained compound with methanesulfonyl chloride or p-toluenesulfonyl chloride to give a compound represented by formula (15)
- 82
- (where Rs is a methanesulfonyl group or a p-toluenesulfonyl group), treating the obtained compound with a halogenating agent so that it is halogenated to give a compound represented by formula (16)
- 83
- (where X1 is a halogen atom), and treating the obtained compound with magnesium to give a compound represented by formula (4)
- 84
- (where X1 is a halogen atom).
9 more elements
A process comprising the steps of treating a compound of formula (2)
- 85
- (where A1 is a protective group) with hexamethylenetetramine in the presence of an acid catalyst and thereafter hydrolyzing the same to produce a compound represented by formula (3)
- 86
- (where A1 is a protective group).
1 more element
A process comprising the steps of treating a compound of formula (9)
- 87
- (where A1 and A2 are each a protective group) with hexamethylenetetramine in the presence of an acid catalyst and thereafter hydrolyzing the same to produce a compound represented by formula (3)
- 88
- (where A1 is a protective group).
1 more element
A process comprising the steps of reacting a compound of formula (3)
- 89
- (where A1 is a protective group) with a metal hydride and thereafter reacting the same with a compound of formula (4)
- 90
- (where X1 is a halogen atom) to give a compound represented by formula (5)
- 91
- (where A1 is a protective group), and recrystallizing the obtained compound of formula (5) in a hydrocarbon or in a lower alcohol/water mixed solvent to give a purified form of the compound of formula (5).
3 more elements
A process comprising the steps of cyclizing a compound represented by formula (5)
- 92
- (where A1 is a protective group) to give a compound represented by formula (6)
- 93
- (where A1 is a protective group), treating the obtained compound of formula (6) with an alkali in a lower alcohol and treating the same with aluminum oxide to give a purified form of the compound of formula (6).
1 more element
A process for producing a compound represented by formula (1)
- 94
- which comprises the fourteenth step of treating a compound of formula (9)
- 95
- (where A1 and A2 are each a protective group) with hexamethylenetetramine in the presence of an acid catalyst and thereafter hydrolyzing the same to give a compound represented by formula (3)
- 96
- (where A1 is a protective group), the third step of reacting the compound of formula (3) with a metal hydride and thereafter reacting the same with a compound represented by formula (4)
- 97
- (where X1 is a halogen atom) to give a compound represented by formula (5)
- 98
- (where A1 is a protective group), the fifth step of cyclizing the compound of formula (5) to give a compound represented by formula (6)
- 99
- (where A1 is a protective group), and the seventh step of deprotecting the compound of formula (6)
- 100
- (where A1 is a protective group) to give a compound represented by formula (1)
- 101
12 more elements
A process for producing a compound represented by formula (1)
- 102
- which comprises the fourteenth step of treating a compound of formula (9)
- 103
- (where A1 and A2 are each a protective group) with hexamethylenetetramine in the presence of an acid catalyst and thereafter hydrolyzing the same to give a compound represented by formula (3)
- 104
- (where A1 is a protective group), the second step of recrystallizing the compound of formula (3) in a lower alcohol/water mixed solvent to give a purified form of the compound of formula (3), the third step of reacting the compound of formula (3) with a metal hydride and thereafter reacting the same with a compound represented by formula (4)
- 105
- (where X1 is a halogen atom) to give a compound represented by formula (5)
- 106
- (where A1 is a protective group), the fourth step of recrystallizing the compound of formula (5) in a hydrocarbon or in a lower alcohol/water mixed solvent to give a purified form of the compound of formula (5), the fifth step of cyclizing the compound of formula (5) to give a compound represented by formula (6)
- 107
- (where A1 is a protective group), the sixth step of treating the compound of formula (6) with an alkali in a lower alcohol and thereafter treating the same with aluminum oxide to give a purified form of the compound of formula (6), and the seventh step of deprotecting the compound of formula (6)
- 108
- (where A1 is a protective group) to give a compound represented by formula (1)
- 109
12 more elements
Dependencies are inferred from the claim text.