Ethanol → ethyl 2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

HRID 840939Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[CH2:10][C:9](=[O:11])[NH:8][C:5]2=[N:6][CH:7]=1.C(N(CC)CC)C.[C]=O.[CH3:21][OH:22].[CH2:23]([OH:25])[CH3:24]>CS(C)=O.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:11]=[C:9]1[NH:8][C:5]2=[N:6][CH:7]=[C:2]([C:21]([O:25][CH2:23][CH3:24])=[O:22])[CH:3]=[C:4]2[CH2:10]1

Participants

Conditions

Temperature: 95 °C

Procedure

To a mixture of 5-bromo-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (213 mg, 1 mmol) in dimethylsulfoxide (1 ml) and ethanol (5 ml) in Parr bomb were added triethylamine (0.31 ml, 2.25 mmol), palladium acetate (33.7 mg, 0.15 mmol), and 1,4-(bisdiphenylphosphino)propane (61.9 mg, 0.15 mmol). Carbon monoxide gas (40 atm) was applied and the reaction mixture was heated at 95° C. for 18 hours with vigorous stirring. The reaction mixture was diluted with diethyl ether (50 ml) and washed with water (10 ml). The aqueous layer was thoroughly extracted with diethyl ether. The combined organic layers were dried over anhydrous MgSO4, filtered and evaporated under vacuum to give crude product. Trituration of the crude product with methanol provided the title compound as a tan solid (53 mg, 26%). 1H NMR (d6-DMSO): δ11.39 (s, 1H), 8.62 (s, 1H), 7.95 (s, 1H),4.27 (q, 2H, J=7 Hz), 3.59 (s, 2H), 1.28 (t, 3H, J=7 Hz). MS (−ve APCI): 205 (4, M−H).

Workup

washwashed with water (10 ml)
extractionThe aqueous layer was thoroughly extracted with diethyl ether
dry with materialThe combined organic layers were dried over anhydrous MgSO4
filtrationfiltered
customevaporated under vacuum
customto give crude product

Sources & evidence

ORD record: ord-cb93634cfe114cb996ea478a04d5ba33
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369086B1

Reaction notes

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