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

HRID 1168230Notes

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): δ 11.39 (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
customThe combined organic layers were dried over
filtrationanhydrous MgSO4, filtered
customevaporated under vacuum
customto give crude product

Sources & evidence

ORD record: ord-c50a142827ea4aac83bcf3de27a8e6ef
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06624171B1

Reaction notes

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