Sodium Hydroxide → 2,6-difluoro-3-(propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide

HRID 2196691Notes

Reaction equation

HRID 2196691 reaction equation
[OH-].[Na+].[F:3][C:4]1[C:21]([N:22](S(CCC)(=O)=O)[S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])=[CH:20][CH:19]=[C:18]([F:35])[C:5]=1[C:6]([NH:8][C:9]1[CH:10]=[C:11]2[CH:17]=[CH:16][NH:15][C:12]2=[N:13][CH:14]=1)=[O:7]>C1COCC1.CO>[F:3][C:4]1[C:21]([NH:22][S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])=[CH:20][CH:19]=[C:18]([F:35])[C:5]=1[C:6]([NH:8][C:9]1[CH:10]=[C:11]2[CH:17]=[CH:16][NH:15][C:12]2=[N:13][CH:14]=1)=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131730122HCID 131730122, compound

Product 1

HCID 441994082,6-difluoro-3-(propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamideYield 45%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 1M solution of NaOH (809 μL, 0.809 mmol) was added to a solution of 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide (135 mg, 0.270 mmol) in 4:1 THF/MeOH (1.4 mL, 0.2M). The reaction mixture was stirred at room temperature for 30 minutes. The majority of the organic solvents were removed in vacuo. The resulting residue was acidified with 1N HCl (0.8 mL) and then partitioned between EtOAc (30 mL) and water (10 mL). The organic layer was washed with water (3×10 mL), brine (10 mL), dried (Na2SO4), filtered and concentrated. The resulting residue was triturated with minimal CH2Cl2, and the precipitate was filtered and rinsed with Et2O to afford 2,6-difluoro-3-(propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide as a solid (48 mg, 45% yield for 2 steps).

Workup

  1. customThe majority of the organic solvents were removed in vacuo
  2. custompartitioned between EtOAc (30 mL) and water (10 mL)
  3. washThe organic layer was washed with water (3×10 mL), brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was triturated with minimal CH2Cl2
  8. filtrationthe precipitate was filtered
  9. washrinsed with Et2O

Sources & evidence

ORD record
ord-5c76efda1111414598b776dc58b13230
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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