Sodium Carbonate → HCID 19040758, compound

HRID 1683916Notes

Reaction equation

HRID 1683916 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[C:19]1[N:26]=[CH:25][CH:24]=[CH:23][C:20]=1[C:21]#[N:22].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[C:21]([C:20]1[C:19]([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])=[N:26][CH:25]=[CH:24][CH:23]=1)#[N:22]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 810792-ChloronicotinonitrileHCID 10376533(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

Product 1

HCID 19040758HCID 19040758, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole and 2-chloronicotinonitrile were used. Sodium carbonate were used as base. N,N-dimethylformamide was used as solvent, and the reaction was heated at 110° C. for 20 hours. Column chromatography afforded the title compound (32%) as an orange amorphous solid: Rf =0.4 in 9:1:0.1 [methylene chloride/methanol/ammonium hydroxide]; 13C NMR (CDCl3) δ157.7, 152.7, 141.7, 134.2, 129.8, 128.1, 123.1, 122.2, 118.7, 116.8, 113.6, 113.2, 111.5, 102.2, 66.6, 57.5, 40.8, 31.5, 30.0, 21.9; FAB HRMS calculated for [C20H21N5.H]332.2073, found 332.1871.

Sources & evidence

ORD record
ord-0da0dc74ad144431b590cc33503dc19e
Source dataset
uspto-grants-1997_06
Patent number
US05639752

Reaction notes

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