Methyl iodide → HCID 57481469, compound

HRID 1960109Notes

Reaction equation

HRID 1960109 reaction equation
I[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[C:9]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[C:22]([F:27])[C:23]([I:26])=[C:24]([F:25])[C:19]=3[NH:18][C:17]2=[S:28])=[CH:11][CH:10]=1>C1COCC1>[C:9]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[C:22]([F:27])[C:23]([I:26])=[C:24]([F:25])[C:19]=3[N:18]=[C:17]2[S:28][CH3:2])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86640504HCID 86640504, compound

Product 1

HCID 57481469HCID 57481469, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Iodomethane (2 M in methyl-text-butyl ether, 22.87 mL, 45.7 mmol) was added to a solution of cesium carbonate (14.9 g, 45.7 mmol) and 1-(biphenyl-4-ylmethyl)-4,6-difluoro-5-iodo-1,3-dihydro-2H-benzimidazole-2-thione (10.94 g, 22.87 mmol) in THF (100 mL). After stirring at rt. overnight, volatiles were removed. Chromatography over silica eluting with 15-60% EtOAc/hexanes afforded the desired product as a beige solid.

Workup

  1. customovernight, volatiles were removed

Sources & evidence

ORD record
ord-da79eff3cf0d42d4a2006d470659f423
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

Loading…