Triethylamine → HCID 19040755, compound

HRID 1683915Notes

Reaction equation

HRID 1683915 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][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH3:17].Br[C:19]1C=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][C:20]=1[N+:31]([O-:33])=[O:32].C([N:36](CC)CC)C>CN(C)C=O>[CH3:17][N:13]1[CH2:14][CH2:15][CH2:16][CH:12]1[CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:19]3[C:20]([N+:31]([O-:33])=[O:32])=[CH:21][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:23][N:36]=3)[CH:3]=2)[NH:7][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1197054-Bromo-3-nitrobiphenylHCID 10376533(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

Product 1

HCID 19040755HCID 19040755, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole and 4-bromo-3-nitrobiphenyl were used. Triethylamine was used as base, N,N-dimethylformamide was used as solvent, and the reaction was heated at 110° C. for 12 hours. Column chromatography afforded the title compound (24%) as a red amorphous solid: 1H NMR (CDCl3) δ9.63 (br s, NH), 8.97 (br s, NH), 8.42 (d, J=2.2 Hz, 1H), 7.56-7.25 (m, 9H), 7.08 (d, J=9.0 Hz, 2H), 3.50-3.32 (m, 2H), 2.95-2.79 (m, 2H), 2.59-2.52 (m, 1H), 2.53 (s, 3H), 2.05-1.71 (m, 4H); 13C NMR (CDCl3) δ144.4, 138.8, 134.9, 134.5, 132.4, 131.1, 130.2, 129.7, 129.0, 127.3, 126.2, 124.7, 124.1, 120.8, 116.7, 115.9, 112.7, 112.0, 67.9, 57.4, 40.6, 31.2, 28.6, 21.9; FAB HRMS calculated for [C26H26N4O2.H]427.2136, found 427.2099.

Sources & evidence

ORD record
ord-e1ec4710d86f4934a38b9707e1309bc5
Source dataset
uspto-grants-1997_06
Patent number
US05639752

Reaction notes

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