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

HRID 2389689Notes

Reaction equation

HRID 2389689 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:39][CH3:40])=[C:6]([CH:38]=1)[CH2:7][N:8]([C:24]([C:26]1[S:30][C:29]2[C:31]([F:36])=[CH:32][CH:33]=[C:34]([F:35])[C:28]=2[C:27]=1[Cl:37])=[O:25])[CH:9]1[CH2:14][CH2:13][CH:12]([N:15]([CH3:23])[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:11][CH2:10]1.[CH2:41]([S:43]([C:46]1[CH:51]=[CH:50][C:49](B(O)O)=[CH:48][CH:47]=1)(=[O:45])=[O:44])[CH3:42]>>[Cl:37][C:27]1[C:28]2[C:34]([F:35])=[CH:33][CH:32]=[C:31]([F:36])[C:29]=2[S:30][C:26]=1[C:24]([N:8]([CH2:7][C:6]1[CH:38]=[C:2]([C:49]2[CH:48]=[CH:47][C:46]([S:43]([CH2:41][CH3:42])(=[O:45])=[O:44])=[CH:51][CH:50]=2)[CH:3]=[CH:4][C:5]=1[O:39][CH3:40])[CH:9]1[CH2:10][CH2:11][CH:12]([N:15]([CH3:23])[C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])[CH2:13][CH2:14]1)=[O:25]

Participants

3

Reactant 2

HCID 27734204-(Ethylsulphonyl)benzeneboronic acidHCID 59683556tert-Butyl {4-[(5-bromo-2-methoxy-benzyl)-(3-chloro-4,7-difluoro-benzo[b]thiophene-2-carbonyl)-amino]-cyclohexyl}-methyl-carbamate

Product 1

HCID 59683486tert-Butyl {4-[(3-chloro-4,7-difluoro-benzo[b]thiophene-2-carbonyl)-(4'-ethanesulfonyl-4-methoxy-biphenyl-3-ylmethyl)-amino]-cyclohexyl}-methyl-carbamate

Procedure

Aryl bromide 220 (200 mg, 0.30 mmol) is coupled to 4-(ethanesulfonyl)-benzene boronic acid (65 mg, 0.30 mmol) using Method A to afford the title compound.

Sources & evidence

ORD record
ord-cc16122cbffd402f9d6795b4c693b465
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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