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

HRID 1787585Notes

Reaction equation

HRID 1787585 reaction equation
C(=O)([O-])[O-].[K+].[K+].C1(S([N:16]2[C:20]3=[CH:21][N: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>[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](=[CH:21][N: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 57600364HCID 57600364, compound

Product 1

HCID 116018673-[2-(Pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-1H-pyrrolo[2,3-c]pyridineYield 64.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add potassium carbonate (40 mg, 0.29 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-c]pyridine (Example 12, Part A; 16 mg, 0.036 mmol) in methanol (3 mL). Reflux the reaction mixture overnight (15 h). Concentrate the mixture in vacuo and purify by silica gel chromatography, using the appropriate mixture of methylene chloride, chloroform, methanol, and concentrated aqueous ammonium hydroxide, to provide 7 mg (64%) of the title compound as a tan solid. MS (ES) m/z=302 (M+H).

Workup

  1. temperatureReflux the reaction mixture overnight (15 h)
  2. concentrationConcentrate the mixture in vacuo
  3. custompurify by silica gel chromatography
  4. additionthe appropriate mixture of methylene chloride, chloroform, methanol, and concentrated aqueous ammonium hydroxide

Sources & evidence

ORD record
ord-b1b9ab84b54c47719578b7db7263db69
Source dataset
uspto-grants-2009_03
Patent number
US07511056B2

Reaction notes

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