Dabco → HCID 178427327, compound

HRID 2173987Notes

Reaction equation

HRID 2173987 reaction equation
Br[C:2](Br)=[CH:3][C:4]1[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:15]([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=[O:17])=[O:16].[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>[CH3:13][C:12]1[C:4]([CH2:3][C:2]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:5]2[C:9](=[C:10]([CH3:14])[CH:11]=1)[N:8]([S:15]([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=[O:16])=[O:17])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 9237DabcoHCID 7372853,4-DiaminobenzonitrileHCID 867015534-(2,2-Dibromovinyl)-5,7-dimethyl-1-tosyl-1H-indole

Product 1

HCID 178427327HCID 178427327, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 4-(2,2-dibromovinyl)-5,7-dimethyl-1-tosyl-1H-indole (130 mg, 0.269 mmol), 3,4-diaminobenzonitrile (46.6 mg, 0.350 mmol), and DABCO (75 mg, 0.673 mmol) in NMP (0.5 mL) was stirred at 100° C. for 19 h. The reaction mixture was cooled to room temperature. The reaction mixture was concentrated and purified by silica gel flash column chromatography (heptanes/EtOAc=1/3 to 0/1) to give the title compound. MS (ESI+) m/z 455.2 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by silica gel flash column chromatography (heptanes/EtOAc=1/3 to 0/1)

Sources & evidence

ORD record
ord-ac086dff35d04b8180ae8523f1224907
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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