Potassium Carbonate → HCID 67155788, compound

HRID 2196688Notes

Reaction equation

HRID 2196688 reaction equation
[F:1][C:2]1[C:29]([NH:30][S:31]([CH2:34][CH2:35][CH3:36])(=[O:33])=[O:32])=[CH:28][CH:27]=[C:26]([F:37])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:15](C)=[CH:14][N:13](S(C3C=CC=CC=3)(=O)=O)[C:10]2=[N:11][CH:12]=1)=[O:5].[C:38]([O-])([O-])=O.[K+].[K+]>CO.O>[F:1][C:2]1[C:29]([NH:30][S:31]([CH2:34][CH2:35][CH3:36])(=[O:33])=[O:32])=[CH:28][CH:27]=[C:26]([F:37])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[CH:15]=[C:14]([CH3:38])[NH:13][C:10]2=[N:11][CH:12]=1)=[O:5]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 67156112HCID 67156112, compound

Product 1

HCID 67155788HCID 67155788, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2,6-Difluoro-N-(3-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (0.654 g, 1.19 mmol) was dissolved in MeOH (9 mL) and water (3 mL). K2CO3 (3.295 g, 23.84 mmol) was added, and the reaction mixture was stirred at reflux overnight. The solution was partitioned between water and EtOAc. The organic layer was washed with water (3×), brine, dried over Na2SO4 and concentrated to a solid. The solid was triturated with DCM to provide 2,6-difluoro-N-(2-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide as a solid (148 mg, 30% for three steps). 1H NMR (400 MHz, DMSO-d6) δ 11.31 (br s, 1H), 10.85 (s, 1H), 9.79 (br s, 1H), 8.31 (br s, 2H), 7.51-7.57 (m, 1H), 7.24-7.29 (m, 2H), 3.11-3.15 (m, 2H), 2.26 (br s, 3H), 1.75-1.80 (m, 2H), 0.98-1.02 (m, 3H); m/z (APCI-neg) M−1=407.2.

Workup

  1. temperatureat reflux overnight
  2. customThe solution was partitioned between water and EtOAc
  3. washThe organic layer was washed with water (3×), brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to a solid
  6. customThe solid was triturated with DCM

Sources & evidence

ORD record
ord-7ae383ba1e734b2d8c4a5b1f2842c3a0
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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