Water → 3-Methylthieno[3,2-b]pyridine

Participants

Reaction Conditions

Reaction Steps

3 reaction vials are prepared: 214 mg of 3-bromo-thieno[3,2-b]pyridine (1.0 mmol) and 180 mg of methylboronic acid (3.0 mmol) are put in the each vial with 4 ml of DME/water/EtOH=7/3/1. 1.5 ml of 2 M Na2CO aq. (3.0 mmol) is added and N2 gas is bubbled in for 15 min. 58 mg of Pd(PPh3)4 (0.05 mmol) is added and each vials are sealed. These vials are heated at 130° C. for 30 min in the microwave. All reaction mixtures are combined, and water and CH2Cl2 are added. The CH2Cl2 layer are separated and dried over Na2SO4 and evaporated. The crude products are applied onto a silica-gel chromatography column (Hexane: AcOEt: 2 M NH3 in MeOH=20:4:1) to give 193 mg of the title compound. Yield 43%. mass spectrum (m/e): 150 (M+1); 1H-NMR (CDCl3): 8.76 (dd, 1H, J=4.7 Hz, 1.5 Hz), 8.20 (dd, 1H, J=8.2 Hz, 1.5 Hz), 7.43 (d, 1H, J=1.2 Hz), 7.29 (dd, 1H, J=8.2 Hz, 4.7 Hz), 2.58 (d, 3H, J=1.2 Hz) ppm.

Provenance & Evidence