Hydrazine → 5-(Benzyloxy)-4-fluoro-2-methyl-1H-indole

HRID 1163052Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10]([F:22])=[C:11]([CH2:18][C:19](=O)[CH3:20])[C:12]([N+:15]([O-])=O)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN>[Ni].CO>[CH2:1]([O:8][C:9]1[C:10]([F:22])=[C:11]2[C:12](=[CH:13][CH:14]=1)[NH:15][C:19]([CH3:20])=[CH:18]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 1-(3-benzyloxy-2-fluoro-6-nitrophenyl)-propan-2-one (9.09 g, 30 mmol) and Raney nickel (˜5 g) in methanol (100 mL) was heated to 40° C. and then a solution of hydrazine in methanol (15 mL) was added dropwise with vigorous stirring over a period of 30 min. After refluxing for 1 h, the reaction mixture was cooled to room temperature, filtered through Celite and concentrated. The crude material was passed through a pad of silica gel eluting with dichloromethane and concentrated in vacuo to provide 5-benzyloxy-4-fluoro-2-methyl-1H-indole (6.1 g, 80%) as a yellowish oil. LC/MS; (M+H)+=256.3+.

Workup

temperatureAfter refluxing for 1 h
temperaturethe reaction mixture was cooled to room temperature
filtrationfiltered through Celite
concentrationconcentrated
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-78e67caf359c4d6b9948281eef2940d0
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820814B2

Reaction notes

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