Sodium borohydride → 3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-imidazo[1,2-a]pyridin-2-one

HRID 215972Notes

Reaction equation

[BH4-].[Na+].[CH3:3][C:4]1[C:12]2[C:11]([CH:13]=[C:14]3[N:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]4=[N:16][C:15]3=[O:23])=[CH:10][S:9][C:8]=2[CH:7]=[CH:6][CH:5]=1>C(O)C.CO>[CH3:3][C:4]1[C:12]2[C:11]([CH2:13][CH:14]3[N:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]4=[N:16][C:15]3=[O:23])=[CH:10][S:9][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a suspension of 121 mg (3.2 mmol) of sodium borohydride in 50 mL of ethanol is added a solution of 624 mg (2.1 mmol) of 3-(4-methyl-benzo[b]thiophen-3-ylmethylene)-imidazo[1,2-a]pyridin-2-one in 50 mL of methanol dropwise at −78° C. After stirring for 15 minutes at −78° C., the reaction mixture is quenched with saturated aqueous ammonium chloride solution at −78° C. The product is extracted with dichloromethane. The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo to give the desired compound.

Workup

customthe reaction mixture is quenched with saturated aqueous ammonium chloride solution at −78° C
extractionThe product is extracted with dichloromethane
dry with materialThe organic layer is dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2469c84c63aa41c5bf5cae7cd24ca3f0
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193214B2

Reaction notes

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