Bromomethyl 2-methoxyphenyl ketone → 3-Cyanomethyl-5-fluoro-2-methyl-7-(2-methoxyphenacyl)pyrrolo[2,3-b]pyridine hydrobromide

HRID 1756094Notes

Reaction equation

HRID 1756094 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].[CH3:15][O:16][C:17]1[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=1[C:19](=[O:22])[CH2:20][Br:21]>C(#N)C.C(OCC)C>[BrH:21].[C:1]([CH2:3][C:4]1[C:12]2[C:7]([N:8]([CH2:20][C:19]([C:18]3[CH:23]=[CH:24][CH:25]=[CH:26][C:17]=3[O:16][CH3:15])=[O:22])[CH:9]=[C:10]([F:13])[CH:11]=2)=[N:6][C:5]=1[CH3:14])#[N:2]

Participants

5

Reactant 2

HCID 123440Bromomethyl 2-methoxyphenyl ketoneHCID 19916787HCID 19916787, compound

Product 1

HCID 199168163-Cyanomethyl-5-fluoro-2-methyl-7-(2-methoxyphenacyl)pyrrolo[2,3-b]pyridine hydrobromideYield 81%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-(cyanomethyl)-5-fluoro-2-methylpyrrolo[2,3-b]pyridine (20 mg, 0.11 mmol) and 2-methoxyphenacyl bromide (30 mg, 0.13 mmol) in acetonitrile (0.2 ml) was refluxed under argon for 6 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 (2 ml), filtered, and washed with diethylether to give 36 mg (81%) of the title compound.

Workup

  1. customto reach room temperature
  2. filtrationfiltered
  3. washwashed with diethylether

Sources & evidence

ORD record
ord-0e6c19c0e7d544b396278c3cd0d2f753
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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