2-Chloro-4'-fluoroacetophenone → 3-Cyanomethyl-5-fluoro-2-methyl-7-[4-fluorophenacyl)pyrrolo[2,3-b]pyridine hydrochloride

HRID 1756092Notes

Reaction equation

HRID 1756092 reaction equation
[C:1]([CH2:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([F:13])[CH:11]=2)[NH:6][C:5]=1[CH3:14])#[N:2].[F:15][C:16]1[CH:25]=[CH:24][C:19]([C:20](=[O:23])[CH2:21][Cl:22])=[CH:18][CH:17]=1>C(#N)C.C(OCC)C>[ClH:22].[C:1]([CH2:3][C:4]1[C:12]2[C:7]([N:8]([CH2:21][C:20]([C:19]3[CH:24]=[CH:25][C:16]([F:15])=[CH:17][CH:18]=3)=[O:23])[CH:9]=[C:10]([F:13])[CH:11]=2)=[N:6][C:5]=1[CH3:14])#[N:2]

Participants

5

Reactant 2

HCID 1202482-Chloro-4'-fluoroacetophenoneHCID 19916787HCID 19916787, compound

Product 1

HCID 199167953-Cyanomethyl-5-fluoro-2-methyl-7-[4-fluorophenacyl)pyrrolo[2,3-b]pyridine hydrochlorideYield 42%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-(cyanomethyl)-5-fluoro-2-methylpyrrolo[2,3-b]pyridine (10mg, 0.053 mmol) and 4-fluorophenacyl chloride (19 mg, 0.11 mmol) in acetonitrile (0.2 ml) was refluxed under argon for 26 h, during which time the initial solution was transformed into a suspension. Then the suspension was allowed to reach room temperature, diluted with diethyl ether (2ml), and filtered. The crystalline product was washed with diethyl ether to give 8 mg (42%) of the title compound.

Workup

  1. customto reach room temperature
  2. filtrationfiltered
  3. washThe crystalline product was washed with diethyl ether

Sources & evidence

ORD record
ord-99d45f1946094bc08aba2e7036baf5b6
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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