Pyridine → HCID 19040733, compound

HRID 1683900Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14].F[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-:25])=[O:24].N1C=CC=CC=1>BrC1C=CC=CC=1>[CH3:15][N:13]([CH3:14])[CH2:12][CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:23]([O-:25])=[O:24])[CH:3]=2)[NH:7][CH:6]=1

Participants

Conditions

Temperature: 156 °C

Procedure

5-Amino-3-(2-dimethylaminoethyl)indole and 2-fluoronitrobenzene were used. Pyridine was used as base, bromobenzene was used as solvent, and the reaction was heated at reflux (156° C.) for 11 hours. Chromatography afforded the title compound (82%) as a dark red solid: mp, 116.0°-117.0° C.; 13C NMR (CD3OD) δ146.7, 136.7, 133.2, 131.0, 129.5, 127.2, 124.7, 121.3, 117.3, 117.2, 117.0, 114.1,113.4, 61.4, 45.4, 24.2; HRMS calculated for C18H20N4O2 324.1588, found 324.1564. Anal. calcd. for C18H20N4O2 1/3H2O: C, 65.44; H, 6.31; N, 16.96. Found: 65.44; H, 5.92; N, 16.69.

Workup

temperaturethe reaction was heated

Sources & evidence

ORD record: ord-eb7e09d05fcb432cbd9382b03df09d99
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05639752

Reaction notes

Loading…