Sodium Carbonate → HCID 53868084, compound

HRID 1419161Notes

Reaction equation

HRID 1419161 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].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[C:21](Cl)[C:20]=1[Cl:29].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[C:21]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[C:5]3[CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH3:17])[C:20]=1[Cl:29]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 286972,3,4-TrichloronitrobenzeneHCID 10376533(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

Product 1

HCID 53868084HCID 53868084, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole and 1,2,3-trichloronitrobenzene were used. Sodium carbonate was used as base, N,N-dimethylformamide was used as solvent, and the reaction was heated at 125° C. for 3 hours. Column chromatography afforded the title compound (60%) as a red solid: Rf =0.4 in 9:1:0.1 [methylene chloride/methanol/ammonium hydroxide]; 1H NMR (CDCl3) δ 8.59 (br s, NH), 8.36 (br s, NH), 7.96 (d, J=9.1 Hz, 1H), 7.23 (d, J=8.6 Hz, 1H), 7.09 (s, 1H), 7.07 (d, J=9.1 Hz, 1H), 6.99 (d, J=1.9 Hz, 1H), 6.81 (dd, J=8.6 and 2.1 Hz, 1H), 3.15-3.05 (m, 2H), 2.54 (dd, J=13.8 and 9.6 Hz, 1H), 2.46-2.33 (m, 1H), 2.40 (s, 3H), 2.22 (dd, J=17.4 and 9.3 Hz, 1H), 1.84-1.48 (m, 4H); FAB HRMS calculated for [C20H20Cl2N4O2.H] 419.1044, found 419.1046.

Sources & evidence

ORD record
ord-017c1bf2fe0146b7854e517c54f3d5d7
Source dataset
uspto-grants-1999_03
Patent number
US05886008

Reaction notes

Loading…