Potassium Carbonate → HCID 67540148, compound

Participants

Reaction Conditions

Reaction Steps

To a nitrogen flushed flask containing 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (prepared from tert-butyl-4-oxopiperidine-1-carboxylate according to the literature: Eastwood, P. R. (2000), Tetrahedron Lett., 3705-3708. 127 mg, 0.410 mmol), K2CO3 (142 mg, 1.02 mmol) and dichloro[1,1′-bis(diphenylphosphino)-ferrocene]palladium(H)dichloromethane adduct (17 mg, 0.020 mmol) was added a solution of 1-Benzenesulfonyl-4-chloro-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.342 mmol) in DMF (3 mL). The mixture was heated at 80° C. for 36 hours. The mixture was cooled to room temperature and partitioned between EtOAc and water. The combined organic layers were washed with saturated aqueous NaHCO3 and brine, dried and concentrated. The residue was purified by flash chromatography on silica gel, eluting with hexanes:EtOAc (2:1) to give 4-(1-Benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.068 g, 45%) as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ 8.37 (d, J=5.2 Hz, 1H), 8.20 (d, J=8.0 Hz, 2H), 7.73 (d, J=4.0 Hz, 1H), 7.56 (m, 1H), 7.49 (m, 2H), 7.03 (d, J=5.2 Hz, 1H), 6.73 (d, J=4.0 Hz, 1H), 6.14 (br s, 1H), 4.12 (m, 2H), 3.65 (m, 2H), 2.55 (m, 2H), 1.50 (s, 9H). LCMS (APCI+) m/z 440 [M+H]+; Rt=3.84 min.

Provenance & Evidence