Pyridine → HCID 19040753, compound

HRID 1683905Notes

Reaction equation

HRID 1683905 reaction equation
N[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.Cl[C:17]1[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:20]=[CH:19][N:18]=1.[N:27]1C=CC=CC=1>CN(C)C=O>[CH3:14][N:13]([CH3:15])[CH2:12][CH2:11][C:6]1[C:5]2[C:9](=[CH:10][CH:2]=[C:3]([NH:27][C:17]3[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:4]=2)[NH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 5898332-Chloro-3-(trifluoromethyl)pyridineHCID 19040754HCID 19040754, compound

Product 1

HCID 19040753HCID 19040753, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
153 °C

Procedure

6-Amino-3-(2-dimethylaminoethyl)indole and 2-chloro-3-trifiuoromethylpyridine were used. Pyridine was used as base, N,N-dimethylformamide was used as solvent, and the reaction was heated at reflux (153° C.) for 18 hours. Chromatography afforded the title compound (10%) as a clear, pale brown oil: 13C NMR (CD3OD) δ155.4, 152.3, 136.9, 136.1, 131.7, 129.0, 124.0, 120.9, 115.7, 113.9, 113.5, 112.5, 110.5, 61.4, 45.4, 24.3; LRMS (m/z, relative intensity) 348 (100, M+), 303 (16), 290 (28), 268 (11), 250 (20); HRMS calculated for C18H19F3N4 348.1564, found 348.1532.

Workup

  1. temperaturethe reaction was heated

Sources & evidence

ORD record
ord-a1de63e96d0d459da3bf34201b9a9aee
Source dataset
uspto-grants-1997_06
Patent number
US05639752

Reaction notes

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