Hydrochloric Acid → N-[3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]-2,5-difluoro-benzenesulfonamide

HRID 60097Notes

Reaction equation

HRID 60097 reaction equation
[NH2:1][C:2]1[C:3]([F:21])=[C:4]([C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([Br:20])[CH:18]=3)[NH:13][CH:12]=2)=[O:10])[C:5]([F:8])=[CH:6][CH:7]=1.N1C=CC=CC=1.[F:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=1[S:36](Cl)(=[O:38])=[O:37].Cl>O1CCCC1>[Br:20][C:17]1[CH:18]=[C:19]2[C:11]([C:9]([C:4]3[C:3]([F:21])=[C:2]([NH:1][S:36]([C:30]4[CH:31]=[C:32]([F:35])[CH:33]=[CH:34][C:29]=4[F:28])(=[O:38])=[O:37])[CH:7]=[CH:6][C:5]=3[F:8])=[O:10])=[CH:12][NH:13][C:14]2=[N:15][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 27369112,5-Difluorobenzenesulfonyl chlorideHCID 58368727(3-Amino-2,6-difluorophenyl)(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)methanone

Product 1

HCID 58368867N-[3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]-2,5-difluoro-benzenesulfonamideYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a reaction flask, (3-amino-2,6-difluoro-phenyl)-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (7, 140 mg, 0.40 mmol) is stirred in 3 mL of tetrahydrofuran and pyridine (0.3 mL, 4.0 mmol) is added, followed by 2,5-difluoro-benzenesulfonyl chloride (25, 127 mg, 0.596 mmol). The reaction is stirred at room temperature for 24 hours, then adjusted to pH 4 with addition of 1M aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer is washed with brine, dried with sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography to provide the desired compound (26, 190 mg, 90%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe resulting material is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-68957b605a214a4abdb83628d3816e6a
Source dataset
uspto-grants-2016_09
Patent number
US09440969B2

Reaction notes

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