Benzyl Alcohol → HCID 71209169, compound

Participants

Reaction Steps

An ice cold solution of 3-(methoxycarbonyl)-1-methyl-1H-indole-2-carboxylic acid (1.0 g, 4.29 mmol) in N,N-dimethylformamide (DMF) (40.5 ml) was treated with diphenylphosphoryl azide (DPPA) (1.016 ml, 4.72 mmol) and Et3N (0.654 ml, 4.72 mmol) and then warmed to ambient temperature. After 2 h, the reaction mixture was treated with benzyl alcohol (0.713 ml, 6.86 mmol) and warmed to 80° C. After 3 h, the reaction mixture was cooled to ambient temperature and partitioned between 1 M HCl and EtOAc. The organic layer was washed with sat. aq. NaHCO3, brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by ISCO (0-50% EtOAc-hexanes) to afford methyl 2-(((benzyloxy)carbonyl)amino)-1-methyl-1H-indole-3-carboxylate (1.15 g, 3.40 mmol, 79% yield) and a yellow oil. The residue was dissolved in MeOH (20 mL), treated with Pd/C (0.362 g, 0.34 mmol) and then purged/backfilled with N2 3× and pressurized to 50 psi of H2. After 18 h, the reaction mixture was filtered and concentrated in vacuo to afford methyl 2-amino-1-methyl-1H-indole-3-carboxylate (426 mg, 2.086 mmol, 48.6% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ=6.98 (m, 4 H), 3.77 (s, 3 H), 3.34 (s, 3 H); LCMS (m/z) ES+=205 (M+1).

Provenance & Evidence