Phenol → HCID 56941485, compound

Participants

Reaction Conditions

Reaction Steps

Phenol (0.12 g, 1.24 mmol) was added to a stirred solution of 2-(chloromethyl)-5-(2-fluorobenzoyl)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine (0.19 g, 0.62 mmol) and K2CO3 (0.25 g, 1.86 mmol) in ACN (5 mL). The reaction mixture was stirred at 80° C. for 16 hours, filtered and the solvent evaporated in vacuo. The crude product was purified by HPLC on a C18 XBridge 30×100 mm, 5 μm column (gradient elution: 0.1% TFA in ACN/0.1% TFA in H2O). The desired fractions were collected and extracted with a saturated solution of NaHCO3 and the aqueous layer extracted with AcOEt. The combined organic layers were dried (Na2SO4), filtered and the solvent evaporated in vacuo to yield 5-(2-fluorobenzoyl)-4,5,6,7-tetrahydro-2-(phenoxymethyl)-thiazolo[5,4-c]pyridine (95 mg, 42% yield) as a solid. C20H17FN2O2S. 1H NMR (DMSO-d6, T=80° C.) δ ppm 2.81 (br. s., 2 H), 3.79 (br. s., 2 H), 4.76 (br. s., 2 H), 5.32 (s, 2 H), 6.85-7.09 (m, 3 H), 7.10-7.28 (m, 4 H), 7.30-7.39 (m, 1 H), 7.40-7.55 (m, 1 H).

Provenance & Evidence