Potassium Phosphate, Tribasic → HCID 66905561, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-1-(6-chlorobenzo[d]thiazol-2-yl)pyrrolidin-3-ol (Reference Example 13a, 0.2547 g, 1.0 mmol), 4-cyanophenylboronic acid (CAS #126747-14-6, 0.2204 g, 1.5 mmol), palladium (II) acetate (2.2 mg, 0.01 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (CAS #657408-07-6, 0.0102 g, 0.025 mmol), and potassium phosphate (0.4246 g, 2.0 mmol) in toluene/isopropanol (2 mL/2 mL) was heated under microwave irradiation at 150° C. for 10 minutes. The reaction mixture was then cooled to room temperature and concentrated under reduced pressure. This residue was partitioned between ethyl acetate and saturated aqueous sodium carbonate. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (80:20 to 60:40 hexane/isopropanol). Fractions containing product were combined and concentrated under reduced pressure to provide (S)-4-(2-(3-hydroxypyrrolidin-1-yl)benzo[d]thiazol-6-yl)benzonitrile. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.91-2.02 (m, 1H), 2.06-2.19 (m, 1H), 3.38-3.46 (m, 1H), 3.56-3.68 (m, 3H), 4.41-4.48 (m, 1H), 5.14 (d, J=4 Hz, 1H), 7.54 (d, J=8 Hz, 1H), 7.68 (dd, J=2, 8 Hz, 1H), 7.89 (s, 1H), 8.23 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 322 (M+H)+.

Provenance & Evidence