Potassium Carbonate → 3-[2-(Pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-1H-pyrrolo[2,3-b]pyridine

HRID 1787583Notes

Reaction equation

HRID 1787583 reaction equation
C(=O)([O-])[O-].[K+].[K+].C1(S([N:16]2[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[C:18]([C:25]3[C:29]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=4)=[N:28][N:27]4[CH2:36][CH2:37][CH2:38][C:26]=34)=[CH:17]2)(=O)=O)C=CC=CC=1>CO.O>[N:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[C:29]1[C:25]([C:18]2[C:19]3[C:20](=[N:21][CH:22]=[CH:23][CH:24]=3)[NH:16][CH:17]=2)=[C:26]2[CH2:38][CH2:37][CH2:36][N:27]2[N:28]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57600363HCID 57600363, compound

Product 1

HCID 116164163-[2-(Pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-1H-pyrrolo[2,3-b]pyridineYield 68%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Add potassium carbonate (21 mg, 0.15 mmol) to a solution of 1-benzenesulfonyl-3-[2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-1H-pyrrolo[2,3-b]pyridine (Example 3, Part A; 34 mg, 0.77 mmol) in methanol/water (0.9 mL/0.3 mL). Reflux the reaction overnight (16 h). Concentrate in vacuo, add aqueous sodium chloride (10 mL), and extract with chloroform (3×25 mL). Dry the combined organic extracts with sodium sulfate, filter, and concentrate in vacuo. Purify by flash column chromatography, using the appropriate mixture of methylene chloride, chloroform, methanol, and concentrated aqueous ammonium hydroxide, to provide 16 mg (68%) of the title compound as an off-white solid. MS (ES) m/z=302 (M+H).

Workup

  1. temperatureReflux
  2. customthe reaction overnight (16 h)
  3. concentrationConcentrate in vacuo
  4. additionadd aqueous sodium chloride (10 mL)
  5. extractionextract with chloroform (3×25 mL)
  6. dry with materialDry the combined organic extracts with sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customPurify by flash column chromatography
  10. additionthe appropriate mixture of methylene chloride, chloroform, methanol, and concentrated aqueous ammonium hydroxide

Sources & evidence

ORD record
ord-aec83f5b9e184fbb9c7e9c8347447d4c
Source dataset
uspto-grants-2009_03
Patent number
US07511056B2

Reaction notes

Loading…