Sodium Carbonate → 3-(3-Methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)isonicotinaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-Methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-0)-3H-benzooxazol-2-one (330 mg, 1.2 mmol), 3-Bromo-pyridine-4-carbaldehyde (186 mg, 1 mmol), polymer bound Pd(PPh3)4 (642 mg, 0.07 mmol), Na2CO3 (2 M in water, 1 mL, 2 mmol) in N,N-Dimethylacetamide (9 mL) and water (1 mL) was heated to 100° C. by microwave for 1 h. The reaction mixture was cooled to room temperature. The suspension was diluted with CH2Cl2 (15 mL) and filtered through a pad of celite. The filtrate was concentrated in vacuo to reddish brown solid. This crude material was purified by flash column (0-10% CH3OH in CH2Cl2, v/v) and afforded 152 mg of the desired product. ESI-MS m/z: 255.0 [M+1]+, Retention time 1.03 min; 1HNMR (DMSO, 400.342 MHz): δ 3.39 (s, 3H), 7.27 (dd, J=8.2, 1.8 Hz, 1H), 7.50 (d, J=8.2 Hz, 1H), 7.57 (d, J=1.8 Hz, 1H), 8.85 (m, 2H), 10.0 (s, 1H).

Provenance & Evidence