Boron tribromide → 3-Cyanomethyl-5-fluoro-2-methyl-7-(2-hydroxyphenacyl)pyrrolo[2,3-b]pyridine

HRID 1756095Notes

Reaction equation

HRID 1756095 reaction equation
Br.[C:2]([CH2:4][C:5]1[C:13]2[C:8]([N:9]([CH2:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24]C)=[O:17])[CH:10]=[C:11]([F:14])[CH:12]=2)=[N:7][C:6]=1[CH3:26])#[N:3].B(Br)(Br)Br>C(Cl)Cl>[C:2]([CH2:4][C:5]1[C:13]2[C:8]([N:9]([CH2:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[OH:24])=[O:17])[CH:10]=[C:11]([F:14])[CH:12]=2)=[N:7][C:6]=1[CH3:26])#[N:3]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 199168163-Cyanomethyl-5-fluoro-2-methyl-7-(2-methoxyphenacyl)pyrrolo[2,3-b]pyridine hydrobromide

Product 1

HCID 199168033-Cyanomethyl-5-fluoro-2-methyl-7-(2-hydroxyphenacyl)pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A mixture of 3-cyanomethyl-5-fluoro-2-methyl-7-(2-methoxyphenacyl)pyrrolo[2,3-b]pyridine hydrobromide (25 mg, 0.06 mmol), methylene chloride (2 ml), and BBr3 in methylene chloride (1M; 0.4 ml) under argon was refluxed for 8 h. The red gum was digested in a methylene chloride aqueous sodium bicarbonate mixture. The organic phase was dried over anhydrous Na2SO4, filtered, and evaporated to give a yellow crystalline product. Yield 19 mg (98%).

Workup

  1. temperaturewas refluxed for 8 h
  2. dry with materialThe organic phase was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customto give a yellow crystalline product

Sources & evidence

ORD record
ord-36c5aa9cb52c473a9cfbd091883c15ff
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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