Carbon tetrabromide → 2-(4-(Bromomethyl)-2-nitrophenyl)-5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine

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Reaction Steps

To a nearly clear solution of (3-nitro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methanol (0.394 g, 0.977 mmol) and triphenyl phosphine (0.294 mL, 1.27 mmol) in 10 mL DCM at 0° C. was added carbon tetrabromide (0.114 mL, 1.17 mmol) in one portion. The reaction mixture was allowed to stir 1 h, then was treated with 3.5 g silica gel and dried. Purification by silica gel chromatography, 40 g, 0-30% EA/hexanes gave 2-(4-(bromomethyl)-2-nitrophenyl)-5-(1-phenylcyclopropyl)thiazolo-[5,4-b]pyridine as an orange-yellow solid. MS (ESI) m/z: Calculated: 467.0; Observed: 467.6 (M++1).

Provenance & Evidence