Dimethylformamide → Fadrozole

HRID 22548

Reaction equation

HRID 22548 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:13]3[CH:14]=[N:15][CH:16]=[C:12]3[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:17][N:18](C)C=O>O>[C:17]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:13]3[CH:14]=[N:15][CH:16]=[C:12]3[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1)#[N:18]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 140971965-(p-Bromophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

Product 1

HCID 59693Fadrozole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 85 mg of 5-(p-bromophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine and 74 mg of cuprous cyanide in 1 ml of N,N-dimethylformamide is heated under nitrogen at 120° for 11 h. The reaction mixture is cooled, diluted with 10 ml of water and extracted with ethyl acetate. The organic extracts are dried over sodium sulfate and evaporated. The resulting oil is chromatographed on silica gel with ethyl acetate to yield the title compound, m.p. 117°-118°.

Workup

  1. temperatureis heated under nitrogen at 120° for 11 h
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic extracts are dried over sodium sulfate
  5. customevaporated
  6. customThe resulting oil is chromatographed on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-00f7638125924cf68d1eb79ce35a532a
Source dataset
uspto-grants-1995_06
Patent number
US05428160

Linked notes

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