Pyridine → HCID 19040764, compound

HRID 1683904Notes

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].N1C=CC=CC=1.F[C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[C:25]#[N:26]>>[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:23]3[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=3[C:25]#[N:26])[CH:3]=2)[NH:7][CH:6]=1

Participants

Reactant 3

HCID 1049Pyridine

HCID 678552-Fluorobenzonitrile2×

HCID 118202113-(2-DIMETHYLAMINO-ETHYL)-1H-INDOL-5-YLAMINE

Product 1

HCID 19040764HCID 19040764, compoundYield 2%

Procedure

5-Amino-3-(2-dimethylaminoethyl)indole and 2-fluorobenzonitrile were used. Pyridine was used as base, 2-fluorobenzonitrile was used as solvent, and the reaction was stirred at reflux for 8 hours. Chromatography afforded the title compound (2%) as a clear, pale brown oil: 1H NMR (CD3OD) δ7.43 (dd, J=7.7 and 1.5 Hz, 1H), 7.38 (d, J=1.9 Hz, 1H), 7.34 (d, J=8.6 Hz, 1H), 7.30-7.23 (m, 1H), 7.07 (s, 1H) 6.97 (dd, J=8.6 and 1.9 Hz, 1H), 6.85 (d, J=8.5 Hz, 1H), 6.73-6.67 (m, 1H), 4.91 (s, 2H), 2.92-2.86 (m, 2H), 2.65-2.59 (m, 2H), 2.30 (s, 6H); HRMS calculated for C19H20N4 304.1690, found 304.1682.

Workup

temperatureat reflux for 8 hours

Sources & evidence

ORD record: ord-172a20df658f48e8b98d51117592220b
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05639752

Reaction notes

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