3-Bromothioanisole → HCID 59683470, compound

HRID 2389671Notes

Reaction equation

HRID 2389671 reaction equation
[C:1]([N:8]([CH3:28])[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][CH3:24])[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Br[C:30]1[CH:31]=[C:32]([S:36][CH3:37])[CH:33]=[CH:34][CH:35]=1.[Cl:38][C:39]1[C:40]2[C:50]([F:51])=[CH:49][CH:48]=[C:47]([F:52])[C:41]=2[S:42][C:43]=1[C:44](Cl)=[O:45]>>[Cl:38][C:39]1[C:40]2[C:50]([F:51])=[CH:49][CH:48]=[C:47]([F:52])[C:41]=2[S:42][C:43]=1[C:44]([N:15]([CH2:16][C:17]1[CH:18]=[C:19]([C:34]2[CH:35]=[CH:30][CH:31]=[C:32]([S:36][CH3:37])[CH:33]=2)[CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH:12]1[CH2:13][CH2:14][CH:9]([N:8]([CH3:28])[C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[CH2:10][CH2:11]1)=[O:45]

Participants

4

Reactant 3

HCID 27356273-BromothioanisoleHCID 219384153-Chloro-4,7-difluorobenzo[b]thiophene-2-carbonyl chlorideHCID 252081913-{[4-(BOC-methyl-amino)-cyclohexylamino]-methyl}-4-methoxy-benzene boronic acid

Product 1

HCID 59683470HCID 59683470, compound

Procedure

Boronic acid 4 (300 mg, 0.77 mmol) is coupled to 3-bromothioanisole (156 mg, 0.77 mmol) using Method A. On filtration of the cooled reaction mixture through celite and removal of the solvents in vacuo, the crude biaryl amine is treated with acid chloride 8 (246 mg, 0.92 mmol) using Method D to give the title compound.

Workup

  1. filtrationOn filtration of the cooled reaction mixture
  2. customthrough celite and removal of the solvents in vacuo

Sources & evidence

ORD record
ord-be8cc99edad94d27967d99ca95a51d4a
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

Loading…