# US 10,246,415 B2 · Process for preparing carbazoles

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- Number: US 10,246,415 B2
- Document ID: US10246415B2
- Status: Granted
- Kind: B2
- Application number: 15/574,051
- Filed: 2016-05-27
- Published: 2018-08-16
- Granted: 2019-04-02
- Earliest claimed: 2015-05-28
- Assignees: Dow Global Technologies LLC
- Applicants: Dow Global Technologies LLC
- Inventors: Chunming Zhang; Arvind Jaganathan; Heqi Pan; Philip Fontaine; Jerzy Klosin
- Web page: https://patentgrep.com/patent/US10246415B2

## CPC

- C07D 209/86: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
- C07D 209/88: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07F 7/083: {Syntheses without formation of a Si-C bond}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

A process for preparing one or more carbazoles comprising (a) contacting one or more compounds represented by formula (1) below with diboron reagents in the presence of PdCl2(dppf) to form one or more 2,2′-dichlorobiaryl represented by formula (2) below; and (b) contacting the one or more 2,2′-dichlorobiaryls with one or more H2N—Y compounds, in the presence of one or more palladium containing catalytic components; thereby forming one or more carbazoles represented by formula (3) below is provided.

## Claims

### Claim 1

A process for preparing a carbazole comprising:
(a) contacting a compound represented by formula (1) below
wherein Cl is a chlorine atom; X is selected from the group consisting of bromo, iodo, triflate (trifluoromethanesulfonate), mesylate (methanesulfonate), arenesulfonates; R1-R4 are selected from the group consisting of hydrogen, alkyls, fluoroalkyls, aryls, heteroaryls, alkoxys, tertiary amines, fluoro, nitrile (CN), nitro (NO2), and trialkyl(aryl)silyl; and R1-R4 are never the same as X with diboron reagents in the presence of PdCl2(dppf) to form a dichlorobiaryl represented by formula (2);
and (b) contacting the 2,2′-dichlorobiaryl represented by formula (2) with a H2N—Y compound, wherein Y is selected from the group consisting of H, —COOR, —C(O)R, SiR3, SiAr3, CH2Ar, Na, Li, and 2-pyrimidyl, wherein Ar is a phenyl group and R is selected from the group consisting of alkyls, aryls, heteroaryls, and alkoxys in the presence of palladium containing catalytic components;
thereby forming the carbazole represented by formula (3) below

### Claim 2 (depends on 1)

The process according to claim 1 wherein Y is tert-butyloxycarbonyl, or H.

### Claim 3 (depends on 1)

The process according to claim 1, wherein the compound represented by formula (1) comprises 2-chloro-4--substituted phenyl trifluoromethanesulfonate where the substituent may be a alkyl, silyl, tertiary amines, or alkoxy.

### Claim 4 (depends on 1)

The process according to claim 1, wherein the compound represented by formula (1) comprises 2-chloro-4-tert-octylphenyl trifluoromethanesulfonate.

### Claim 5 (depends on 1)

The process according to claim 1, wherein the carbazole comprises tert-butyl 2,7-di-tert-octyl-9H-carbazole-9-carboxylate.

### Claim 6 (depends on 1)

The process according to claim 1, wherein the carbazole is selected from the group consisting of 2,7-disubstituted carbazoles, -1,8-disubstituted carbazoles; 3,6-disubstituted carbazoles, and 4,5-disubstituted carbazoles.