Phenacyl bromide → 3-(Cyanomethyl)-5-fluoro-2-methyl-7-phenacylpyrrolo[2,3-b]pyridine hydrobromide

HRID 1756087Notes

Reaction equation

HRID 1756087 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].[CH2:15]([Br:24])[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17]>C(#N)C>[BrH:24].[C:1]([CH2:3][C:4]1[C:12]2[C:7]([N:8]([CH2:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:17])[CH:9]=[C:10]([F:13])[CH:11]=2)=[N:6][C:5]=1[CH3:14])#[N:2]

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 19916787HCID 19916787, compound

Product 1

HCID 199168203-(Cyanomethyl)-5-fluoro-2-methyl-7-phenacylpyrrolo[2,3-b]pyridine hydrobromideYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3- (cyanomethyl)-5-fluoro-2-methylpyrrolo [2,3-b]pyridine (0.28 g, 1.5 mmol) and phenacyl bromide 0.32 g, 1.6 mmol) in acetonitrile (5 ml) was refluxed under argon for 3 h, during which time the initial solution was transformed into a suspension. Then the suspension was cooled in an ice bath, filtered and washed with diethyl ether (2×2 ml). The crystalline product was purified by recrystallization from hot acetonitrile to give 0.52 g (90% ) of the title compound.

Workup

  1. temperatureThen the suspension was cooled in an ice bath
  2. filtrationfiltered
  3. washwashed with diethyl ether (2×2 ml)
  4. customThe crystalline product was purified by recrystallization from hot acetonitrile

Sources & evidence

ORD record
ord-5879f7c4c13e4d778b50aabf120b8135
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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