Pyridine → HCID 57771786, compound

Participants

Reaction Steps

Add oxalyl chloride (10 mL, 114.6 mmol) and DMF (4 drops) to a stirring suspension of 4′-fluoro-biphenyl-4-carboxylic acid (4.9 g, 22.7 mmol) in CH2Cl2 (150 mL). Stir the reaction mixture at room temperature for 3 h. Concentrate the mixture in vacuo, add n-hexane, re-concentrate, and re-dissolve in CH2Cl2. Add the resultant 4′-fluoro-biphenyl-4-carbonyl chloride solution to a mixture of 2-chloro-benzothiazol-6-ylamine (3.31 g, 17.9 mmol) and pyridine (3.0 mL) in CH2Cl2 (150 mL). Stir the reaction mixture overnight at room temperature. Dilute the reaction mixture with CH2Cl2. Wash the reaction mixture twice with 1.0M HCl and once with 1.0M NaOH. Dry the mixture over Na2SO4, concentrate in vacuo, and triturate with MeOH to yield the desired product (6.34 g, 93%). 1H NMR (400 MHz, DMSO-d6): δ10.59 (s, 1H), 8.69 (d, J=1.6 Hz, 1H), 8.09 (d, J=8.0 Hz, 2H), 7.96 (d, J=8.8 Hz, 1H), 7.87-7.79 (m, 5H), 7.38-7.31 (m, 2H).

Provenance & Evidence