Methanol → (3-Nitro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methanol

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Reaction Steps

To a 0° C. solution of methyl 3-nitro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzoate (1.10 g, 2.5 mmol) in THF and methanol (0.31 mL, 7.6 mmol) was added lithium borohydride, 2.0 M solution in tetrahydrofuran (1.9 mL, 3.8 mmol). The reaction mixture was stirred at ambient temp, and upon completion the reaction mixture was cooled to 0° C. was quenched with ice and sat'd aq. NH4Cl carefully. The reaction mixture was partitioned between DCM and sat'd aq. NH4Cl and extracted with DCM. The combined organics were purified by silica gel chromatography, EA/hexanes gradient, to give (3-nitro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methanol as an orage solid. MS (ESI) m/z: Calculated: 403.1; Observed: 403.8 (M++1).

Provenance & Evidence