o-Fluoro-beta-nitrostyrene → Benzyl 3-(1-(2-fluorophenyl)-2-nitroethyl)-1H-indol-6-ylcarbamate

HRID 2361257Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:8]=2)[CH:3]=[CH:2]1.[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1/[CH:28]=[CH:29]/[N+:30]([O-:32])=[O:31]>ClCCl>[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH:28]([C:3]1[C:4]2[C:9](=[CH:8][C:7]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:6][CH:5]=2)[NH:1][CH:2]=1)[CH2:29][N+:30]([O-:32])=[O:31]

Participants

Conditions

Temperature: 105 °C

Procedure

Benzyl 1H-indol-6-ylcarbamate (0.981 g, 3.68 mmol) and (E)-1-fluoro-2-(2-nitrovinyl)benzene (0.770 g, 4.60 mmol) were suspended and well mixed in dichloromethane (15 mL). The suspension was concentrated under vacuum to dryness. The solid mixture was then heated at 105° C. under nitrogen for 7 hr. The mixture was subjected to ISCO (120 g silica gel, solid loading, 20-45% ethyl acetate) to afford the desired product (1.287 g, 2.97 mmol, 81% yield) as a white solid.

Workup

concentrationThe suspension was concentrated under vacuum to dryness

Sources & evidence

ORD record: ord-da96014e59594580abfe3d40e9bb1bf8
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685969B2

Reaction notes

Loading…