3-Bromobenzonitrile → tert-Butyl {4-[(3'-cyano-4-ethoxy-biphenyl-3-ylmethyl)-amino]-cyclohexyl}-methyl-carbamate

HRID 2389608Notes

Reaction equation

HRID 2389608 reaction equation
[C:1]([N:8]([CH3:29])[CH:9]1[CH2:14][CH2:13][CH:12]([NH:15][CH2:16][C:17]2[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][C:22]=2[O:23][CH2:24][CH3:25])[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Br[C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=1)[C:34]#[N:35]>>[C:34]([C:33]1[CH:32]=[C:31]([C:19]2[CH:20]=[CH:21][C:22]([O:23][CH2:24][CH3:25])=[C:17]([CH2:16][NH:15][CH:12]3[CH2:13][CH2:14][CH:9]([N:8]([CH3:29])[C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[CH2:10][CH2:11]3)[CH:18]=2)[CH:38]=[CH:37][CH:36]=1)#[N:35]

Participants

3

Reactant 2

HCID 233813-BromobenzonitrileHCID 596835893-{[4-(BOC-methyl-amino)-cyclohexylamino]-methyl}-4-ethoxy-benzene boronic acid

Product 1

HCID 59683463tert-Butyl {4-[(3'-cyano-4-ethoxy-biphenyl-3-ylmethyl)-amino]-cyclohexyl}-methyl-carbamate

Procedure

Boronic acid 11 (374 mg, 0.92 mmol) is coupled to 3-bromobenzonitrile (200 mg, 1.10 mmol) using Method B to give the title compound.

Sources & evidence

ORD record
ord-3b045ab386d44dfb9c7ebb4f953b474e
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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