Dabco → HCID 178427328, compound

HRID 2174049Notes

Reaction equation

HRID 2174049 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:25])[C:5]([CH:21]=[C:22](Br)Br)=[C:6]2[C:10]=1[N:9]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2.[NH2:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[NH2:35])[C:30]#[N:31].C1N2CCN(CC2)C1>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:25])[C:5]([CH2:21][C:22]2[NH:35][C:34]3[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][C:27]=3[N:26]=2)=[C:6]2[C:10]=1[N:9]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 9237DabcoHCID 7372853,4-DiaminobenzonitrileHCID 867016717-Chloro-4-(2,2-dibromovinyl)-5-methyl-1-tosyl-1H-indole

Product 1

HCID 178427328HCID 178427328, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 7-chloro-4-(2,2-dibromovinyl)-5-methyl-1-tosyl-1H-indole (67 mg, 0.133 mmol), 3,4-diaminobenzonitrile (26.6 mg, 0.200 mmol) and DABCO (44.8 mg, 0.399 mmol) in NMP (0.5 mL) was stirred at 110° C. After stirring overnight, the reaction mixture was loaded onto silica gel and was purified by flash chromatography (0-100% EtOAc in heptanes) to provide 2-((7-chloro-5-methyl-1-tosyl-1H-indol-4-yl)methyl)-1H-benzo[d]imidazole-5-carbonitrile. The obtained compound was dissolved in EtOH (5.0 mL), and KOH (0.118 g, 2.105 mmol) and isoamylamine (0.489 mL, 4.21 mmol) were added, and the mixture was stirred at 100° C. in the microwave for 30 minutes. The reaction mixture was loaded onto silica gel and was purified by flash chromatography (0-100% EtOAc in heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.50 (s, 1H) 11.33 (br. s., 1H) 7.93 (s, 1H) 7.57 (d, J=8.84 Hz, 1H) 7.47 (dd, J=8.34, 1.52 Hz, 1H) 7.33 (t, J=2.78 Hz, 1H) 7.06 (s, 1H) 6.52-6.63 (m, 1H) 4.45 (s, 2H) 2.39 (s, 3H). HRMS calcd. for C18H13ClN4 (M+H)+ 321.0902. found 321.0906.

Workup

  1. customwas purified by flash chromatography (0-100% EtOAc in heptanes)

Sources & evidence

ORD record
ord-613b7927d2734859b263e32d892857eb
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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