Sodium Carbonate → HCID 11336470, compound

Participants

Reaction Conditions

Reaction Steps

A solution of [(4-bromophenyl)(methylsulfonyl)amino]acetic acid (intermediate 3, 20 mg, 65 μmol) in dimethoxyethane (1 mL) was added in one portion to a mixture of 4-cyanophenyl-boronic acid (9.5 mg, 65 μmol) and fibrecat FC1001 (2.71% Pd; 25 mg, 6.5 μmol) in a Smith microwave reaction vial. Aqueous sodium carbonate solution (1.0 M; 130 μL, 130 μmol) was added and the vial capped. The crude reaction mixture was heated at 150° C. for 15 min using a Smith Synthesiser microwave reactor. On cooling the vial was opened and the contents were filtered through a Whatman 5 μM filter tube, washing the filter cake with methanol (2×1 mL). The filtrate was evaporated and the resulting residue was purified using mass directed auto-preparative reverse phase HPLC to give the title compound (1.1 mg, 5%) as a white solid. LC/MS: 2.94 min; z/e 329, calcd (M−1) 329. 1H NMR (400 MHz: MeOD): 7.80 (4H), 7.75 (2H), 7.65 (2H), 4.45 (2H), 3.10 (3H).

Provenance & Evidence