Reaction #166527

Reaction equation

N-(3-ethyl-1-((6-(((2R,3S)-3-hydroxypyrrolidin-2-yl)methoxy)pyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HCHO

NaBH(OAc)3

→

final product

Yield 77.7%

N-(3-ethyl-1-((6-(((2R,3S)-3-hydroxy-1-methylpyrrolidin-2-yl)methoxy)pyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Yield 77.7%

Solvents

MeOH

Conditions

Workup

1. 1
   Concentrationconcentrated under reduced pressure
2. 2
   Otherpurified by silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1)

Procedure

To N-(3-ethyl-1-((6-(((2R,3S)-3-hydroxypyrrolidin-2-yl)methoxy)pyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (5 mg, 0.0098 mmol; prepared as in Example 36) in MeOH (1 mL) was added HCHO as a 35% aqueous solution (16 mg, 0.20 mmol) and NaBH(OAc)3 (10 mg, 0.049 mmol). The reaction mixture was stirred for 30 minutes, concentrated under reduced pressure and purified by silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1) to provide the final product (4 mg). MS (ES+APCI) m/z=526 (M+H).

Source