Water → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine

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Reaction Steps

To a solution of potassium tert-butoxide (4.02 g, 35.8 mmol) in 100 mL DMSO under nitrogen was added trimethyl sulfoxonium iodide (7.89 g, 35.8 mmol) in 4 portions over about 20 minutes. 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylvinyl)thiazolo[5,4-b]pyridine (10.0 g, 23.9 mmol) was suspended in 150 mL THF and filtered through a glass frit, rinsing with 25 mL THF. The filtrate was added to the reaction dropwise very slowly from an addition funnel over 1.5-2 h. The resulting orange reaction was allowed to stir 30 min, at which point the THF was removed in vacuo, resulting in a precipitate. Water and ice was added slowly with stirring (approximately 400 mL total). The solid was isolated by filtration rinsing with water and MeOH. The solid was dried in vacuo to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine as a light orange solid. MS (ESI) m/z: Calculated: 432.1; Observed: 433.1 (M++1).

Provenance & Evidence