o-Fluoro-beta-nitrostyrene → 4-(3-(1-(2-Fluorophenyl)-2-nitroethyl)-1H-indol-6-yl)morpholine

HRID 2361237Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[CH:8]=2)[CH:3]=[CH:2]1.[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1/[CH:23]=[CH:24]/[N+:25]([O-:27])=[O:26]>C1(C)C=CC=CC=1>[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH:23]([C:3]1[C:4]2[C:9](=[CH:8][C:7]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)=[CH:6][CH:5]=2)[NH:1][CH:2]=1)[CH2:24][N+:25]([O-:27])=[O:26]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-(1H-indol-6-yl)morpholine (0.300 g, 1.483 mmol) and (E)-1-fluoro-2-(2-nitrovinyl)benzene (0.372 g, 2.225 mmol) in toluene (8 mL) was heated in a pressure tube at 150° C. for 2 days. The solvent was removed under vacuum, and the residue was subjected to ISCO (80 g silica gel, solid loading, 30-60% ethyl acetate/hexane) to provide the desired product (0.239 g, 0.647 mmol, 43.6% yield) as a tan solid.

Workup

customThe solvent was removed under vacuum

Sources & evidence

ORD record: ord-47656450c45b418b82aba30895acf1c3
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685969B2

Reaction notes

Loading…