Water → HCID 44223282, compound

HRID 2196659Notes

Reaction equation

HRID 2196659 reaction equation
[F:1][C:2]1[C:30]([NH:31][S:32]([CH2:35][CH2:36][CH3:37])(=[O:34])=[O:33])=[CH:29][CH:28]=[C:27]([F:38])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:15]([CH:16]=[CH2:17])=[CH:14][N:13](S(C3C=CC=CC=3)(=O)=O)[C:10]2=[N:11][CH:12]=1)=[O:5].O.C([O-])([O-])=O.[K+].[K+]>CO.[Pd]>[CH2:16]([C:15]1[C:9]2[C:10](=[N:11][CH:12]=[C:7]([NH:6][C:4](=[O:5])[C:3]3[C:27]([F:38])=[CH:28][CH:29]=[C:30]([NH:31][S:32]([CH2:35][CH2:36][CH3:37])(=[O:34])=[O:33])[C:2]=3[F:1])[CH:8]=2)[NH:13][CH:14]=1)[CH3:17]

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 67155901HCID 67155901, compound

Product 1

HCID 44223282HCID 44223282, compoundYield 37.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2,6-Difluoro-N-(1-(phenylsulfonyl)-3-vinyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (0.0093 g, 0.017 mmol) was dissolved in MeOH (1.0 mL). 10% Pd/C (2.0 mg) was added and followed by stirring under a balloon of H2 for 1 hour. Water (0.3 mL) and K2CO3 (0.0235 g, 0.170 mmol) were added, and the reaction mixture was stirred at 50° C. for 18 hours. The organic portion was washed with water (3×), brine, dried over Na2SO4 and concentrated. The resulting residue was purified by column chromatography (1:2 hexane/EtOAc) giving N-(3-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (2.7 mg, 37.6%). 1H NMR (400 MHz, DMSO-d6) δ 11.33 (br s, 1H), 10.84 (s, 1H), 9.79 (br s, 1H), 8.32-8.34 (m, 2H), 7.51-7.57 (m, 1H), 7.24-7.27 (m, 2H), 3.10-3.14 (m, 2H), 2.67-2.73 (m, 2H), 1.74-1.80 (m, 2H), 1.25-1.28 (m, 2H), 0.98-1.01 (m, 3H); m/z (APCI-neg) M−1=421.2.

Workup

  1. stirringthe reaction mixture was stirred at 50° C. for 18 hours
  2. washThe organic portion was washed with water (3×), brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified by column chromatography (1:2 hexane/EtOAc)

Sources & evidence

ORD record
ord-94372a48f6124c4dac527d26e68a1a42
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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