4-Bromothioanisole → HCID 59683524, compound

HRID 2389672Notes

Reaction equation

HRID 2389672 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:35]=[CH:34][C:33]([S:36][CH3:37])=[CH:32][CH:31]=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:30]2[CH:35]=[CH:34][C:33]([S:36][CH3:37])=[CH:32][CH:31]=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 660374-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 59683524HCID 59683524, compound

Procedure

Boronic acid 4 (200 mg, 0.51 mmol) is coupled to 4-bromothioanisole (104 mg, 0.51 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 (163 mg, 0.61 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-058726e41d884058bf9a258b0c33ae49
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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