4'-Bromo-2,2,2-trifluoroacetophenone → tert-Butyl (4-{(3-chloro-4,7-difluoro-benzo[b]thiophene-2-carbonyl)-[4-methoxy-4'-(2,2,2-trifluoro-acetyl)-biphenyl-3-ylmethyl]-amino}-cyclohexyl)-methyl-carbamate

HRID 2389636Notes

Reaction equation

HRID 2389636 reaction equation
[C:1]([N:8]([CH3:42])[CH:9]1[CH2:14][CH2:13][CH:12]([N:15]([CH2:30][C:31]2[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][C:36]=2[O:37][CH3:38])[C:16]([C:18]2[S:22][C:21]3[C:23]([F:28])=[CH:24][CH:25]=[C:26]([F:27])[C:20]=3[C:19]=2[Cl:29])=[O:17])[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Br[C:44]1[CH:49]=[CH:48][C:47]([C:50](=[O:55])[C:51]([F:54])([F:53])[F:52])=[CH:46][CH:45]=1>>[Cl:29][C:19]1[C:20]2[C:26]([F:27])=[CH:25][CH:24]=[C:23]([F:28])[C:21]=2[S:22][C:18]=1[C:16]([N:15]([CH2:30][C:31]1[CH:32]=[C:33]([C:44]2[CH:49]=[CH:48][C:47]([C:50](=[O:55])[C:51]([F:53])([F:54])[F:52])=[CH:46][CH:45]=2)[CH:34]=[CH:35][C:36]=1[O:37][CH3:38])[CH:12]1[CH2:11][CH2:10][CH:9]([N:8]([CH3:42])[C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[CH2:14][CH2:13]1)=[O:17]

Participants

3

Reactant 2

HCID 6038664'-Bromo-2,2,2-trifluoroacetophenoneHCID 596835093-{[[4-(BOC-methyl-amino)-cyclohexyl]-(3-chloro-4,7-difluoro-benzo[b]thiophene-2-carbonyl)-amino]-methyl}-4-methoxy-benzene boronic acid

Product 1

HCID 59683541tert-Butyl (4-{(3-chloro-4,7-difluoro-benzo[b]thiophene-2-carbonyl)-[4-methoxy-4'-(2,2,2-trifluoro-acetyl)-biphenyl-3-ylmethyl]-amino}-cyclohexyl)-methyl-carbamate

Procedure

Boronic acid 9 (250 mg, 0.40 mmol) is coupled to 4′-bromo-2,2,2-trifluoroacetophenone (120 mg, 0.48 mmol) using Method B to give the title compound.

Sources & evidence

ORD record
ord-151f0e4fc2e441518c189bb72171c6ad
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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