Hydrochloric Acid → N-{3-[(4-Cyano-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-4-trifluoromethyl-benzenesulfonamide

HRID 1091903Notes

Reaction equation

HRID 1091903 reaction equation
[NH:1]1[C:5]2[N:6]=[CH:7][CH:8]=[C:9]([C:10]#[N:11])[C:4]=2[CH:3]=[CH:2]1.[F:12][C:13]1[C:18]([CH:19]=[O:20])=[C:17]([F:21])[CH:16]=[CH:15][C:14]=1[NH:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=1)(=[O:25])=[O:24].[OH-].[K+].Cl>CO>[C:10]([C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:1][CH:2]=[C:3]([CH:19]([OH:20])[C:18]3[C:13]([F:12])=[C:14]([NH:22][S:23]([C:26]4[CH:27]=[CH:28][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:31]=4)(=[O:25])=[O:24])[CH:15]=[CH:16][C:17]=3[F:21])[C:4]=12)#[N:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 117151961H-pyrrolo(2,3-b)pyridine-4-carbonitrileHCID 58086928HCID 58086928, compound

Product 1

HCID 59487256N-{3-[(4-Cyano-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-4-trifluoromethyl-benzenesulfonamideYield 9.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a round bottom flask 1H-pyrrolo[2,3-b]pyridine-4-carbonitrile (5, 0.054 g, 0.38 mmol), N-(2,4-difluoro-3-formyl-phenyl)-4-trifluoromethyl-benzenesulfonamide (4, 0.179 g, 0.49 mmol), 0.75 mL of methanol and potassium hydroxide (0.103 g, 1.89 mmol) were combined. The reaction was stirred at room temperature for 46 hours, then neutralized with 0.1 N aqueous hydrochloric acid and extracted 3× with ethyl acetate. The organic layers were combined and washed with brine, then dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The material was purified by silica gel column chromatography eluting with ethyl acetate and hexane. The appropriate fractions were combined and the solvent removed under vacuum to provide the desired compound (6, 0.018 g). MS (ESI) [M+H+]+=509.1.

Workup

  1. extractionextracted 3× with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe material was purified by silica gel column chromatography
  7. washeluting with ethyl acetate and hexane
  8. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-fd599e8bf30043eeaf150f9de6cdc22f
Source dataset
uspto-grants-2012_03
Patent number
US08129404B2

Reaction notes

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