Water → (5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-(2-fluoro-3-methoxy-phenyl)-methanone

HRID 1964967Notes

Reaction equation

HRID 1964967 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[Cl-].[Cl-].[Cl-].[Al+3].[F:15][C:16]1[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19].O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:18]([C:17]3[CH:21]=[CH:22][CH:23]=[C:24]([O:25][CH3:26])[C:16]=3[F:15])=[O:19])=[CH:6][NH:7][C:8]2=[N:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 269863302-Fluoro-3-methoxybenzoyl chloride

Product 1

HCID 57595715(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-(2-fluoro-3-methoxy-phenyl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 5-bromo-1H-pyrrolo[2,3-b]pyridine (67, 2.00 g, 0.0102 mol) in methylene chloride (120 mL), under an atmosphere of nitrogen, was added aluminum trichloride (8.20 g, 0.0615 mol). The reaction was stirred at room temperature for 60 minutes, then 2-fluoro-3-methoxy-benzoyl chloride (34, 2.12 g, 0.0112 mol, prepared from the corresponding carboxylic acid using the protocol of Example 1, Scheme 13, Step 4), dissolved in methylene chloride (20.0 mL), was added. After 2 hours, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified by silica gel chromatography, eluting with 25% ethyl acetate in hexane to provide P-0265 (approx 2.6 g, 73%). MS (ESI) [M−H+]+=347, 349.

Workup

  1. additionwas added
  2. waitAfter 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography
  8. washeluting with 25% ethyl acetate in hexane
  9. customto provide P-0265 (approx 2.6 g, 73%)

Sources & evidence

ORD record
ord-096c3984cdfa4403bb7160ef285133dd
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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