Potassium Carbonate → HCID 44223227, compound

HRID 2196656Notes

Reaction equation

HRID 2196656 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].C([O-])([O-])=O.[K+].[K+]>CO.O>[F:1][C:2]1[C:30]([NH:31][S:32]([CH2:35][CH2:36][CH3:37])(=[O:33])=[O:34])=[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][NH:13][C:10]2=[N:11][CH:12]=1)=[O:5]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 67155901HCID 67155901, compound

Product 1

HCID 44223227HCID 44223227, compoundYield 61.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2,6-Difluoro-N-(1-(phenylsulfonyl)-3-vinyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (0.0061 g, 0.0109 mmol) was dissolved in MeOH (1.0 mL) and water (0.3 mL). K2CO3 (0.0150 g, 0.109 mmol) was added, and the reaction mixture was stirred at room temperature overnight. The solution was partitioned between water and EtOAc. The organic portion was washed with water (3×), brine, dried over Na2SO4 and concentrated. The resulting residue was purified by column chromatography (1:1 hexane/EtOAc/1% HCO2H) to give 2,6-difluoro-3-(propylsulfonamido)-N-(3-vinyl-1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide (2.8 mg, 61.2%). 1H NMR (400 MHz, DMSO-d6) δ 11.81 (br s, 1H), 10.92 (s, 1H), 9.80 (br s, 1H), 8.61-8.62 (m, 1H), 8.44-8.45 (m, 1H), 7.65-7.67 (m, 1H), 7.52-7.58 (m, 1H), 7.24-7.29 (m, 1H), 6.81-6.88 (m, 1H), 5.56-5.61 (m, 1H), 5.11-5.14 (m, 1H), 3.10-3.14 (m, 2H), 1.74-1.80 (m, 2H), 0.98-1.02 (m, 3H); m/z (APCI-neg) M−1=419.3.

Workup

  1. customThe solution was partitioned between water and EtOAc
  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 (1:1 hexane/EtOAc/1% HCO2H)

Sources & evidence

ORD record
ord-c3790159f8344ac2ad54ce11b02eadfb
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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