Allyl bromide → 5-(biphenyl-4-yl)-6-chloro-2-(methylsulfonyl)-1-(prop-2-en-1-yl)-1H-benzimidazole

HRID 340768Notes

Reaction equation

[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:19]([Cl:20])=[CH:18][C:10]3[NH:11][C:12]([S:14]([CH3:17])(=[O:16])=[O:15])=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:33](Br)[CH:34]=[CH2:35]>C1COCC1>[C:1]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:19]([Cl:20])=[CH:18][C:10]3[N:11]([CH2:35][CH:34]=[CH2:33])[C:12]([S:14]([CH3:17])(=[O:15])=[O:16])=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 5-biphenyl-4-yl-6-chloro-2-(methylsulfonyl)-1H-benzimidazole (1.72 g, 4.49 mmol) in THF (30 ml) and 1M potassium carbonate (3.10 g, 22.46 mmol) was added allyl bromide (0.6 ml, 6.89 mmol). The reaction mixture was heated to 60° C. for 20 h. Then the volatiles were removed in vacuo and the resulting residue was partitioned between EtOAc and water. The aqueous phase was separated and extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated. Chromatography of the resulting residue over silica eluting with 20-40% EtOAc/hexanes afforded the desired product. LC-MS: calculated for C23H19ClN2O2S 422.09, observed m/e: 422.94 (M+H)+ (Rt 2.52/4 min).

Workup

customThen the volatiles were removed in vacuo
customthe resulting residue was partitioned between EtOAc and water
customThe aqueous phase was separated
extractionextracted with EtOAc
washThe combined organic layers were washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-0d3968ba877f42ec9f191199549538eb
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895596B2

Reaction notes

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