Water → Ethanone, 2-bromo-1-(4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-

HRID 2108735Notes

Reaction equation

HRID 2108735 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[Cl-].[Al+3].[Cl-].[Cl-].[Br:15][CH2:16][C:17](Br)=[O:18].O>ClCCl>[Br:15][CH2:16][C:17]([C:10]1[C:3]2[C:4](=[N:5][CH:6]=[CH:7][C:2]=2[F:1])[NH:8][CH:9]=1)=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) ChlorideHCID 112979984-Fluoro-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 57421973Ethanone, 2-bromo-1-(4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluoro-1H-pyrrolo[2,3-b]pyridine (2.00 g, 0.0147 mol) (Org. Lett., 2003, 5, 5023-5025) in dichloromethane was added aluminum chloride (3.92 g, 0.0294 mol) in portions, the mixture was stirred at RT for 30 min, then bromoacetyl bromide (4.45 g, 0.022 mol) was added dropwise. The reaction mixture was stirred at 50° C. for 1 h, when TLC indicated no starting material. To the reaction mixture was added 150 mL water, and the resulting suspension was heated at 100° C. for 1 h, then filtered to afford the desired product, 90% pure. H NMR, DMSO-d6: 4.72(s, 2H), 7.12(m, 1H), 8.36(m, 1H), 8.67(s, 1H).

Workup

  1. stirringThe reaction mixture was stirred at 50° C. for 1 h
  2. temperaturethe resulting suspension was heated at 100° C. for 1 h
  3. filtrationfiltered

Sources & evidence

ORD record
ord-f43fced1acc84e01a9a38feb9f7b5cd7
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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