Water → Propane-1-sulfonic acid {3-[(5-bromo-1H-pyrrolo[2,3-b]-pyridin-3-yl)-hydroxy-methyl]-2-fluoro-phenyl}-amide

HRID 250593Notes

Reaction equation

HRID 250593 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.[F:11][C:12]1[C:17]([CH:18]=[O:19])=[CH:16][CH:15]=[CH:14][C:13]=1[NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:23])=[O:22].[OH-].[K+].O>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:18]([OH:19])[C:17]3[C:12]([F:11])=[C:13]([NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:23])=[O:22])[CH:14]=[CH:15][CH:16]=3)=[CH:6][NH:7][C:8]2=[N:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 58086814Propane-1-sulfonic acid (2-fluoro-3-formyl-phenyl)-amide

Product 1

HCID 58086504Propane-1-sulfonic acid {3-[(5-bromo-1H-pyrrolo[2,3-b]-pyridin-3-yl)-hydroxy-methyl]-2-fluoro-phenyl}-amideYield 45.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 5-bromo-7-azaindole 67 (312 mg, 1.58 mmol) in methanol (28 mL) were added propane-1-sulfonic acid (2-fluoro-3-formyl-phenyl)-amide (503, 370 mg, 1.5 mmol) and potassium hydroxide (422.8 mg, 7.5 mmol) under an atmosphere of nitrogen. The reaction was stirred at room temperature overnight, then poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give the desired compound as white solid (504, 300 mg, 45.0%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5d8eef28289d438d855bc739f432fe2f
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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