Sodium Carbonate → HCID 59596028, compound

Participants

Reaction Steps

A mixture of compound 1e (15.00 g), 2,4-dichloropyrimidine (7.56 g) and tetrakis(triphenylphosphine)palladium(0) (4.51 g) in a solution of ethylene glycol dimethyl ether (200 mL) and aqueous Na2CO3 (2M, 60 mL) was refluxed overnight. The reaction was quenched with water and extracted with ethyl acetate. The combined organic phase was concentrated and the residue was purified on silica gel column (eluted with 100% dichloromethane and 3% acetone in dichloromethane) to provide 1-benzenesulfonyl-3-(2-chloro-pyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridine (1f) (7.83 g, 54%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.78 (d, J=8.0 Hz, 1H), 8.62 (d, J=5.6 Hz, 1H), 8.52 (d, J=4.8 Hz, 1H), 8.47 (s, 1H), 8.28 (d, J=7.6 Hz, 2H), 7.63 (t, J=7.6 HZ, 1H), 7.57 (d, J=5.2 Hz, 1H), 7.53 (t, J=8.0 Hz, 2H), 7.35 (dd, J=8.0 Hz, 4.8 Hz, 1H). MS (ESI) m/z: 371 (M+H)+.

Provenance & Evidence