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

HRID 1895474Notes

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-a77d255ee86b47249a5fbb74e6dffe3d
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513293B2

Reaction notes

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