Ammonium formate → HCID 59300541, compound

Participants

Reaction Steps

4-Allyl-5-(benzyloxy)-1-methyl-1H-indole (250.0 mg, 0.90 mmol) (Example 59) was dissolved in EtOH (15 mL), then 20% palladium (II) hydroxide on carbon (30 mg) was added, followed by ammonium formate (455 mg, 7.21 mmol). After stirring for 1 h at rt, the mixture was heated to 40° C. for 2.5 h. After cooling to rt, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. Water was added to the residue, and the aqueous phase was extracted with EtOAc (2×). The combined organic phases were dried over Na2SO4, filtered, and concentrated under reduced pressure to give 150 mg (88%) of the title compound as an oil. 1H NMR (400 MHz, CDCl3): δ 1.02 (t, 3H), 1.73 (m, 2H), 2.85 (t, 2H), 3.76 (s, 3H), 4.33 (br, 1H), 6.40 (s, 1H), 6.78 (d, 1H), 7.02 (m, 2H).

Provenance & Evidence