Dimethylformamide → HCID 68711881, compound

HRID 1896549Notes

Reaction equation

HRID 1896549 reaction equation
[OH:1][C:2]1[C:14]2[C:13]3C=[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#N)=[CH:4][N:3]=1.[C:21]([O-])([O-])=O.[K+].[K+].CI.[NH4+].[Cl-].[CH3:31][N:32]([CH:34]=O)[CH3:33]>CCOC(C)=O.O>[CH3:21][O:1][C:2]1[C:14]2[C:13]3[CH:8]=[CH:9][C:10]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:33]=3[N:32]([CH3:31])[C:34]=2[C:5]([C:6]#[N:7])=[CH:4][N:3]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 178510358HCID 178510358, compound

Product 1

HCID 68711881HCID 68711881, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1-hydroxy-7-(trifluoromethyl)-5H-pyrido[4,3-b]indole-4-carbonitrile (Example 5, Step 3) and K2CO3 (2.5 equiv) in DMF (0.09 M) at room temperature was added MeI (1.5 equiv). After stirring at room temperature for 30 min, saturated NH4Cl solution was added along with H2O, and EtOAc (same amount as DMF). The resulting suspension was stirred vigorously for 10 min, and the product was then collected by filtration to give the title compound as a beige solid.

Workup

  1. stirringThe resulting suspension was stirred vigorously for 10 min
  2. filtrationthe product was then collected by filtration

Sources & evidence

ORD record
ord-75fc1aba628441e2a8b0aabdce20157d
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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