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

HRID 2389616Notes

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

Participants

Reactant 2

HCID 7466p-Bromoacetophenone

HCID 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 59683585tert-Butyl {4-[(4'-acetyl-4-methoxy-biphenyl-3-ylmethyl)-(3-chloro-4,7-difluoro-benzo[b]thiophene-2-carbonyl)-amino]-cyclohexyl}-methyl-carbamate

Procedure

Boronic acid 9 (700 mg, 1.12 mmol) is coupled to 4′-bromoacetophenone (268 mg, 1.34 mmol) using Method A to give the title compound.

Sources & evidence

ORD record: ord-281f6626915e4e49afa3591d2c1c2fec
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273747B2

Reaction notes

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