(Chloromethyl)dimethylisopropoxysilane → 1-[6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazol-5-yl]-2-(isopropoxy-dimethyl-silanyl)-ethanol

HRID 1176909Notes

Reaction equation

Cl[CH2:2][Si:3]([CH3:9])([CH3:8])[O:4][CH:5]([CH3:7])[CH3:6].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:19]([CH:28]=[O:29])=[CH:20][C:21]3[NH:25][CH:24]=[N:23][C:22]=3[C:26]=2[F:27])=[C:13]([Cl:30])[CH:12]=1>C1COCC1>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:19]([CH:28]([OH:29])[CH2:2][Si:3]([O:4][CH:5]([CH3:7])[CH3:6])([CH3:9])[CH3:8])=[CH:20][C:21]3[NH:25][CH:24]=[N:23][C:22]=3[C:26]=2[F:27])=[C:13]([Cl:30])[CH:12]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of the Grignard reagent prepared from Mg and chloromethyl dimethylisopropoxy silane (Org. Synth. 1992, 69, 96) [4.4 mL, 3.26 mmol, 0.74 M solution (based on 90% purity)] in THF, is added a solution of 6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazole-5-carbaldehyde 10f (200 mg, 0.54 mmol) in THF (1 mL) at −78° C. After stirring for 1 hour at −78° C., the reaction is quenched with saturated aqueous NH4Cl, and extracted with EtOAc. The organic layer is dried over MgSO4, filtered, concentrated in vacuo to afford the crude desired product which is directly used without further purification.

Workup

customthe reaction is quenched with saturated aqueous NH4Cl
extractionextracted with EtOAc
dry with materialThe organic layer is dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-93e575a9710c48dd8f545ea08d12592d
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842816B2

Reaction notes

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