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

HRID 840922Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.C(N([CH2:17][CH3:18])CC)C.[C]=O.[CH3:21][OH:22].CS(C)=[O:25]>C(O)C.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:21]([C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2)([O:25][CH2:17][CH3:18])=[O:22]

Participants

Conditions

Temperature: 95 °C

Procedure

To a mixture of 5-bromo-7-azaoxindole (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 1,3-(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 vigorously 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. Trituation of the crude product with methanol yielded 5-(carboethoxy)-7-azaoxindole as a tan solid (53 mg, 25.7%). 1H NMR (DMSO-d6): 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-213f487bfc0148cba91e2436b5db15ac
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369086B1

Reaction notes

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