Acetic Anhydride → N-{3-[5-(1-acetyl-1H-indazol-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-2,4-difluoro-phenyl}-2,5-difluoro-benzenesulfonamide

HRID 60099Notes

Reaction equation

HRID 60099 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[F:8][C:9]1[C:14]([C:15]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[C:23]([C:26]4[CH:27]=[C:28]5[C:32](=[CH:33][CH:34]=4)[NH:31][N:30]=[CH:29]5)[CH:24]=3)[NH:19][CH:18]=2)=[O:16])=[C:13]([F:35])[CH:12]=[CH:11][C:10]=1[NH:36][S:37]([C:40]1[CH:45]=[C:44]([F:46])[CH:43]=[CH:42][C:41]=1[F:47])(=[O:39])=[O:38]>O.C(OCC)(=O)C>[C:1]([N:31]1[C:32]2[C:28](=[CH:27][C:26]([C:23]3[CH:24]=[C:25]4[C:17]([C:15]([C:14]5[C:9]([F:8])=[C:10]([NH:36][S:37]([C:40]6[CH:45]=[C:44]([F:46])[CH:43]=[CH:42][C:41]=6[F:47])(=[O:39])=[O:38])[CH:11]=[CH:12][C:13]=5[F:35])=[O:16])=[CH:18][NH:19][C:20]4=[N:21][CH:22]=3)=[CH:34][CH:33]=2)[CH:29]=[N:30]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 53261782N-(2,4-difluoro-3-[5-(1H-indazol-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-2,5-difluoro-benzenesulfonamide

Product 1

HCID 58368896N-{3-[5-(1-acetyl-1H-indazol-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-2,4-difluoro-phenyl}-2,5-difluoro-benzenesulfonamideYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into a reaction flask, a mixture of acetic anhydride (12 mg, 0.11 mmol) and N-{2,4-difluoro-3-[5-(1H-indazol-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-2,5-difluoro-benzenesulfonamide (P-0002, 22 mg, 0.031 mmol) is stirred at room temperature overnight, then diluted with water and ethyl acetate. The organic layer is washed with saturated sodium bicarbonate, then brine and dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with methanol and dichloromethane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (P-0005, 3 mg, 20%). MS (ESI) [M+H+]+=607.8.

Workup

  1. washThe organic layer is washed with saturated sodium bicarbonate
  2. dry with materialbrine and dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting material is purified by silica gel column chromatography
  6. washeluting with methanol and dichloromethane
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0a84a81692d14a27967ddfcbf98924f4
Source dataset
uspto-grants-2016_09
Patent number
US09440969B2

Reaction notes

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