5-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-2-methylbenzenamine → HCID 59436067, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,5-dichloro-9-fluorobenzo[c]-2,6-naphthyridine (Example 1, Step 5) (150 mg, 0.56 mmol) and 5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylaniline (155 mg, 0.62 mmol) in THF (9.3 mL) was added sodium tert-butoxide (65 mg, 0.67 mmol). The reaction stirred at 60° C. for 30 minutes was then quenched by the addition of sat. aq. NaHCO3 solution. The mixture was extracted with EtOAc and the extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by silica gel column chromatography (0-50% EtOAc/heptane) afforded the title compound.

Provenance & Evidence