Method for producing thioether compound

A method for producing a thioether compound or its salt of a general formula:

• wherein R1, Y1, R6, R7, R8, n1, n2 or a group of a general formula:
• have the same meanings as mentioned below,
• which comprises reacting an aryl or heteroaryl compound or its salt of a general formula [III]
• wherein R1 represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having from 1 to 10 carbon atoms, an alkoxy group having from 1 to 10 carbon atoms, an alkylthio group having from 1 to 10 carbon atoms, an alkylsulfinyl group having from 1 to 10 carbon atoms, an alkylsulfonyl group having from 1 to 10 carbon atoms, a hydroxyl group, a carboxyl group, an alkoxycarbonyl group having from 2 to 10 carbon atoms, an alkanoyloxy group having from 2 to 10 carbon atoms, an aryl group, an arylcarbonyl group, an arylcarbonyloxy group, a heteroaryl group, a heteroarylcarbonyl group, a heteroarylcarbonyloxy group, a nitro group, an alkanoylamino group having from 1 to 10 carbon atoms, an arylcarbonylamino group, a heteroarylcarbonylamino group, or an alkanoyl group having from 1 to 10 carbon atoms;
• Y1 represents an alkylene group having from 1 to 6 carbon atoms of which the carbon chain may have a group selected from a sulfur atom, a sulfinyl group, a sulfonyl group, an oxygen atom, a carbonyl group, an oxycarbonyl group, a carbonyloxy group or a group of a general formula:
• wherein R2 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a benzyl group, a phenyl group, a naphthyl group or a pyridyl group;
• X represents a bromine atom, a chlorine atom, a trifluoromethanesulfonyloxy group, a methylsulfonyloxy group, a benzenesulfonyloxy group, a toluenesulfonyloxy group or a nitrobenzenesulfonyloxy group;
• n1 indicates 0 or 1;
• the group of a general formula:
• means an aryl ring group or a heteroaryl ring group;
• provided that when X is a chlorine atom, then the group of a general formula:
• wherein R1, n1 and Y1 have the same meanings as above] is an electron-withdrawing group,
• with a thiol compound or its salt of a general formula [II]:
• wherein R6 and R7 may be the same or different, each representing a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, an amino group, or a phenyl group;
• n2 indicates from 0 to 6;
• R8 represents a hydrogen atom, a halogen atom, a cyano group, an amino group, an alkyl group having from 1 to 10 carbon atoms, a trimethylsilyl group, an alkoxy group having from 1 to 10 carbon atoms, an alkylthio group having from 1 to 10 carbon atoms, an alkylsulfinyl group having from 1 to 10 carbon atoms, an alkylsulfonyl group having from 1 to 10 carbon atoms, a hydroxyl group, a carboxyl group, an alkoxycarbonyl group having from 2 to 10 carbon atoms, an alkanoyloxy group having from 2 to 10 carbon atoms, an aryl group, an arylcarbonyl group, an arylcarbonyloxy group, a heteroaryl group, a heteroarylcarbonyl group, a heteroarylcarbonyloxy group, a nitro group, an alkanoylamino group having from 1 to 10 carbon atoms, an arylcarbonylamino group, a heteroarylcarbonylamino group, an alkanoyl group having from 1 to 10 carbon atoms, or a group of a general formula:
• wherein Y2 represents an alkylene group having from 1 to 6 carbon atoms of which the carbon chain may have a group selected from a sulfur atom, a sulfinyl group, a sulfonyl group, an oxygen atom, a carbonyl group, an oxycarbonyl group, a carbonyloxy group, and a group of a general formula:
• wherein R7 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a benzyl group, a phenyl group, a naphthyl group or a pyridyl group;
• n3 indicates 0 or 1;
• R9 represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a nitro group, an alkyl group having from 1 to 10 carbon atoms, an alkoxy group having from 1 to 10 carbon atoms, an alkylthio group having from 1 to 10 carbon atoms, an alkylsulfinyl group having from 1 to 10 carbon atoms, an alkylsulfonyl group having from 1 to 10 carbon atoms, a hydroxyl group, a carboxyl group, an alkoxycarbonyl group having from 2 to 10 carbon atoms, an alkanoyloxy group having from 2 to 10 carbon atoms, an aryl group, an arylcarbonyl group, an arylcarbonyloxy group, a heteroaryl group, a heteroarylcarbonyl group, a heteroarylcarbonyloxy group, a nitro group, an alkanoylamino group having from 1 to 10 carbon atoms, an arylcarbonylamino group, a heteroarylcarbonylamino group, or an alkanoyl group having from 1 to 10 carbon atoms;
• the group of a general formula:
• means an aryl ring group or a heteroaryl ring group,
• in the presence of a palladium compound selected from a group consisting of palladium acetate, Pd2(dba)3 and Pd(dba)2,
• a base selected from a group consisting of cesium carbonate, amine derivatives of a general formula:
• wherein R3, R4 and R5 may be the same or different, each representing an alkyl group having from 1 to 6 carbon atoms, a benzyl group, a phenyl group or a pyridyl group,
• 1,5-diazabicyclo[4.3.0]non-5-ene and 1,8-diazabicyclo[5.4.0]undec-7-ene,
• and a phosphorus compound selected from a group consisting of a compound of a formula:
• a compound of a formula:
• a compound of a formula:
• a compound of a formula:
• a compound of a formula:
• a compound of a formula:
• a compound of a formula:
• a compound of a formula:
• a compound of a formula:
• a compound of a formula:
• and a compound of a formula: