Ammonium Hydroxide → HCID 16112858, compound

HRID 1896506Notes

Reaction equation

HRID 1896506 reaction equation
Cl[C:2]1[C:14]2[C:13]3[CH:12]=[CH:11][C:10]([C:15]([F:18])([F:17])[F:16])=[CH:9][C:8]=3[NH:7][C:6]=2[C:5]([C:19]#[N:20])=[CH:4][N:3]=1.[NH4+:21].[OH-:22].O([Si](C)(C)C)[K]>CCO>[NH2:21][C:2]1[C:14]2[C:13]3[CH:12]=[CH:11][C:10]([C:15]([F:18])([F:17])[F:16])=[CH:9][C:8]=3[NH:7][C:6]=2[C:5]([C:19]([NH2:20])=[O:22])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 59198428HCID 59198428, compoundHCID 178504318HCID 178504318, compound

Product 1

HCID 16112858HCID 16112858, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1-chloro-7-(trifluoromethyl)-5H-pyrido[4,3-b]indole-4-carbonitrile in a 3:2 (v/v) mixture of EtOH and conc. NH4OH (0.06 M) was heated at 150° C. for 2 h in a stainless steel pressure vessel. After cooling at room temperature, an excess of KOSiMe3 was added and the mixture was heated at 150° C. for 18 h. The reaction mixture was extracted with EtOAc and H2O. After evaporation of the organic solvent the residue was purified by flash chromatography (10% MeOH in EtOAc) to provide the title compound as a white solid.

Workup

  1. temperatureAfter cooling at room temperature
  2. temperaturethe mixture was heated at 150° C. for 18 h
  3. extractionThe reaction mixture was extracted with EtOAc and H2O
  4. customAfter evaporation of the organic solvent the residue
  5. customwas purified by flash chromatography (10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-46efcea418d6483abbb236c942c1a0ec
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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