Acetaldehyde → 6-((6,7-bis(methoxy)-4-quinolinyl)oxy)-N-ethyl-1-methyl-1H-indazol-3-amine

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Reaction Steps

To a stirred solution of 6-((6,7-bis(methyloxy)-4-quinolinyl)oxy)-1-methyl-1H-indazol-3-amine (Example 120, 140 mg, 0.40 mmol) in dry DCM (Aldrich, 4.0 mL) at RT were added acetaldehyde (Aldrich, 21.1 mg, 0.48 mmol) followed by NaHB(OAc)3 (Aldrich, 102 mg, 0.48 mmol). After being stirred for 4 h at RT, the reaction was quenched by addition of water. The aqueous layer was extracted with DCM. The organic layer was dried with MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (DCM/acetone: 100/0 to 60/40) afforded the title compound. MS (ESI, pos. ion) m/z: 379.3 (M+1). Mass Calc'd for C21H22N4O3: 378.43.

Provenance & Evidence