4-(Trifluoromethyl)aniline → HCID 11582157, compound

HRID 1176667Notes

Reaction equation

HRID 1176667 reaction equation
Cl[C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[F:20])[CH2:15]Br.[F:21][C:22]([F:31])([F:30])[C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1>CCOC(C)=O.CCOCC>[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[F:20])[CH2:15][N:6]1[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=[C:2]1[NH:27][C:26]1[CH:28]=[CH:29][C:23]([C:22]([F:21])([F:30])[F:31])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 99644-(Trifluoromethyl)anilineHCID 785722-ChlorobenzimidazoleHCID 5814364-(Bromomethyl)-1,2-difluorobenzene

Product 1

HCID 11582157HCID 11582157, compound

Reagents, catalysts & solvents 1

HCID 21584169Diethylether ethylacetateSolvent

Procedure

The title compound was prepared by Procedure B in two steps from 2-chloro-benzimidazole, 3,4-difluorobenzyl bromide and 4-trifluoromethylaniline. The product was isolated by preparative LCMS and recrystallization (EtOAc/Et2O) to give the title compound as the free base (off-white solid, mp 167-170° C.). MS(ES+) m/z 404 ([M+1]+, 100). 1NMR (DMSO-d6) δ 5.55 (s, 2H), 6.90-6.97 (m, 1H), 7.02-7.13 (m, 2H), 7.25-7.50 (m, 4H), 7.65-7.71 (m, 2H), 8.04-8.12 (m, 2H), 9.55 (s, 1H).

Sources & evidence

ORD record
ord-971134a1b063496da853a475ac19af30
Source dataset
uspto-grants-2010_11
Patent number
US07842817B2

Reaction notes

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