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

HRID 1952207Notes

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.C(OCC)(=O)C>[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 at 20° C. for 20 hours and then for a further 48 hours while adding, on 4 occasions, an additional 100 μl of osmium tetroxide and 80 mg of sodium periodate. The reaction mixture is poured into 50 ml of water and extraction is carried out twice with 50 ml of ethyl acetate. The combined organic phases are washed with a saturated aqueous sodium chloride solution, separated by settling, dried and concentrated to dryness under reduced pressure. The residue is chromatographed on silica, elution being carried out 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

additionfor a further 48 hours while adding, on 4 occasions
washThe combined organic phases are washed with a saturated aqueous sodium chloride solution
customseparated
customdried
concentrationconcentrated to dryness under reduced pressure
customThe residue is chromatographed on silica, elution
additionbeing carried out with a mixture of cyclohexane and ethyl acetate (gradient from 0 to 50%)

Sources & evidence

ORD record: ord-db62c9ba5a374572b953d92a8caf996b
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404848B2

Reaction notes

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