HCID 66801667, compound → HCID 66801420, compound

Participants

Reaction Conditions

Reaction Steps

Iron powder (7.95 g, 141 mmol) was added to a solution of 2-(2-chloro-6-nitrophenyl)-7-fluorothiazolo[5,4-c]pyridine (4.35 g, 14.1 mmol) in AcOH (130 mL). The reaction mixture was heated at 100° C. for 30 minutes and then allowed to cool to room temperature. The volatiles were removed under reduced pressure and the resultant residue was dissolved in DCM/MeOH and filtered through Celite® washing the filter pad thoroughly with further DCM/MeOH. The filtrate was concentrated under reduced pressure and the resultant residue was purified by column chromatography on silica gel eluting with 0-5% MeOH in DCM to afford the title compound as a yellow solid (3.63 g, 92% yield). 1H NMR (300 MHz, CDCl3): δ 9.03 (s, 1H), 8.52 (d, J=2.4 Hz, 1H), 7.16 (t, J=8.2 Hz, 1H), 6.89 (d, J=7.8 Hz, 1H), 6.75 (d, J=8.3 Hz, 1H), 6.28 (br s, 2H). LCMS (Method D): RT=3.51 min, m/z: 280 [M+H+].

Provenance & Evidence