Methanol → 7-Chloro-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetonitrile

HRID 1937318Notes

Reaction equation

HRID 1937318 reaction equation
CC(C)(C)[O-].[K+].[N+:7](CS(C1C=CC(C)=CC=1)(=O)=O)#[C-:8].[Cl:20][C:21]1[CH:22]=[CH:23][C:24]2[C:25]3[C:34]([CH:35]=O)=[N:33][N:32]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:31](=[O:43])[C:26]=3[N:27]([CH3:30])[C:28]=2[CH:29]=1.CO>COCCOC>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]2[C:25]3[C:34]([CH2:35][C:8]#[N:7])=[N:33][N:32]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:31](=[O:43])[C:26]=3[N:27]([CH3:30])[C:28]=2[CH:29]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 161915Tosylmethyl isocyanideHCID 154619027-Chloro-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 154619037-Chloro-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetonitrile

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
-60 °C

Procedure

1.27 g (10.96 mmol) of potassium 1,1-dimethylethoxide are added, in small portions, to a solution of 2.14 g (10.96 mmol) of 1-[(isocyanomethyl)-sulphonyl]-4-methylbenzene in 50 ml of 1,2-dimethoxyethane, the reaction mixture is stirred for 30 min at −60° C., 2.88 g (8.53 mmol) of 7-chloro-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxaldehyde are added and the reaction mixture is stirred for 3 h 30 min at −60° C. 9 ml of methanol are added and the reaction mixture is again stirred for 30 min at room temperature and for 1 h under reflux.

Workup

  1. stirringthe reaction mixture is stirred for 3 h 30 min at −60° C
  2. stirringthe reaction mixture is again stirred for 30 min at room temperature and for 1 h
  3. temperatureunder reflux

Sources & evidence

ORD record
ord-e1080a0cdbb8465799927ce0fef51c5f
Source dataset
uspto-grants-2002_05
Patent number
US06395729B1

Reaction notes

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