Water → 6-formyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

HRID 2363728Notes

Reaction equation

[C:1]1([NH:7][C:8]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15]([CH:18]=C)=[CH:14][N:13]3[CH:20]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I([O-])(=O)(=O)=[O:22].[Na+].C(O)(C)(C)C.O>C1COCC1.[Os](=O)(=O)(=O)=O>[CH:18]([C:15]1[CH:16]=[CH:17][C:12]2[N:13]([CH:20]=[C:10]([C:8]([NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:9])[N:11]=2)[CH:14]=1)=[O:22]

Participants

Conditions

Temperature: 20 °C

Procedure

A suspension of 150 mg of N-phenyl-6-vinylimidazo[1,2-a]pyridine-2-carboxamide, 232 μL of osmium tetroxide and 167.5 mg of sodium periodate in a mixture of 6 mL of THF, 3 mL of t-butanol and 3 mL of water is stirred for 20 hours at 20° C. and then for a further 48 hours while adding in four portions 100 μL of osmium tetroxide and 80 mg of sodium periodate. The reaction mixture is poured into 50 mL of water and the resulting mixture is extracted twice with 50 mL of ethyl acetate. The combined organic phases are washed with saturated aqueous sodium chloride solution, separated by settling, dried and concentrated to dryness under reduced pressure. The residue is chromatographed on silica, eluting with a mixture of cyclohexane and ethyl acetate (gradient from 0 to 50%) to give 100 mg of 6-formyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid

Workup

extractionthe resulting mixture is extracted twice with 50 mL of ethyl acetate
washThe combined organic phases are washed with saturated aqueous sodium chloride solution
customseparated
customdried
concentrationconcentrated to dryness under reduced pressure
customThe residue is chromatographed on silica
washeluting with a mixture of cyclohexane and ethyl acetate (gradient from 0 to 50%)

Sources & evidence

ORD record: ord-6c51fd4a29d743ff8003153a00759f1b
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691990B2

Reaction notes

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