Dabco → HCID 178436212, compound

HRID 2174052Notes

Reaction equation

HRID 2174052 reaction equation
Br[C:2](Br)=[CH:3][C:4]1[C:12]([CH3:13])=[CH:11][C:10]([CH:14]=[CH2:15])=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:16]([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17].[NH2:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[NH2:36])[C:31]#[N:32].C1N2CCN(CC2)C1>CN1C(=O)CCC1>[CH3:13][C:12]1[C:4]([CH2:3][C:2]2[NH:36][C:35]3[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][C:28]=3[N:27]=2)=[C:5]2[C:9](=[C:10]([CH:14]=[CH2:15])[CH:11]=1)[N:8]([S:16]([C:19]1[CH:20]=[CH:21][C:22]([CH3:23])=[CH:24][CH:25]=1)(=[O:17])=[O:18])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 9237DabcoHCID 7372853,4-DiaminobenzonitrileHCID 86701673HCID 86701673, compound

Product 1

HCID 178436212HCID 178436212, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 4-(2,2-dibromovinyl)-5-methyl-1-tosyl-7-vinyl-1H-indole (57 mg, 0.115 mmol) and 3,4-diaminobenzonitrile (23 mg, 0.173 mmol) and DABCO (38.7 mg, 0.345 mmol) in NMP (0.5 mL) was stirred at 110° C. After 80 minutes the mixture was slowly cooled to room temperature overnight, and then heated again at 110° C. for 4 hours. The reaction was cooled to room temperature and loaded onto silica gel and purified by flash chromatography (0-100% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 467.2 (M+H).

Workup

  1. temperatureheated again at 110° C. for 4 hours
  2. temperatureThe reaction was cooled to room temperature
  3. custompurified by flash chromatography (0-100% EtOAc in heptanes)

Sources & evidence

ORD record
ord-76e39e26b513484fb667267e11edcf2c
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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