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

HRID 751314Notes

Reaction equation

HRID 751314 reaction equation
C(=O)([O-])[O-].[K+].[K+].C1(S([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=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>C1(C)C=CC=CC=1>[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:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[NH:16][CH:17]=2)=[C:26]2[CH2:38][CH2:37][CH2:36][N:27]2[N:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22242641Methanol--water (1/1)HCID 586119411-Benzenesulfonyl-3-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-1H-indole

Product 1

HCID 100176853-[2-(Pyridin-2-yl)-5,6-dihydro-4H-pyrrolo [1,2-b]pyrazol-3-yl]-1H-indole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add potassium carbonate (75 mg, 0.55 mmol) to a solution of 1-benzenesulfonyl-3-[2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-1H-indole (120 mg, 0.27 mmol) in 3:1 methanol/water (1.2 mL). Reflux the reaction mixture for 16 h, cool to room temperature, and add toluene (50 mL). Concentrate in vacuo and purify by flash column chromatography, using the appropriate mixture of methylene chloride, chloroform, methanol, and concentrated aqueous ammonium hydroxide, to provide 6 mg (3% over 2 steps) of the title compound as a yellow solid.

Workup

  1. temperatureReflux the reaction mixture for 16 h
  2. concentrationConcentrate in vacuo
  3. custompurify by flash column chromatography
  4. additionthe appropriate mixture of methylene chloride, chloroform, methanol, and concentrated aqueous ammonium hydroxide

Sources & evidence

ORD record
ord-d4df39fe651f43a28ec79a811fd261e8
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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