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

HRID 2389584Notes

Reaction equation

[C:1]([N:8]([CH3:41])[CH:9]1[CH2:14][CH2:13][CH:12]([N:15]([CH2:28][C:29]2[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][C:34]=2[O:35][CH2:36][CH3:37])[C:16]([C:18]2[S:22][C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[C:19]=2[Cl:27])=[O:17])[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Br[C:43]1[CH:48]=[CH:47][C:46]([C:49](=[O:51])[CH3:50])=[CH:45][CH:44]=1>>[C:49]([C:46]1[CH:47]=[CH:48][C:43]([C:31]2[CH:32]=[CH:33][C:34]([O:35][CH2:36][CH3:37])=[C:29]([CH2:28][N:15]([C:16]([C:18]3[S:22][C:21]4[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=4[C:19]=3[Cl:27])=[O:17])[CH:12]3[CH2:13][CH2:14][CH:9]([N:8]([CH3:41])[C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[CH2:10][CH2:11]3)[CH:30]=2)=[CH:44][CH:45]=1)(=[O:51])[CH3:50]

Participants

Reactant 2

HCID 7466p-Bromoacetophenone

HCID 596834943-{[[4-(BOC-methyl-amino)-cyclohexyl]-(3-chloro-benzo[b]thiophene-2-carbonyl)-amino]-methyl}-4-ethoxy-benzene boronic acid

Product 1

HCID 59683640tert-Butyl {4-[(4'-acetyl-4-ethoxy-biphenyl-3-ylmethyl)-(3-chloro-benzo[b]thiophene-2-carbonyl)-amino]-cyclohexyl}-methyl-carbamate

Procedure

Boronic acid 12 (200 mg, 0.33 mmol) is coupled to 4′-bromoacetophenone (79 mg, 0.39 mmol) using Method B to give the title compound.

Sources & evidence

ORD record: ord-9ce3537f58e54bd1b94a20cb4ddd536d
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273747B2

Reaction notes

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