Potassium Carbonate → 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 45580

Reaction equation

HRID 45580 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([N:14]1[CH:18]=[C:17]([C:19]2[C:27]3[C:22](=[N:23][CH:24]=[C:25]([C:28]4[CH:29]=[N:30][N:31]([CH3:33])[CH:32]=4)[CH:26]=3)[N:21](C(OC(C)(C)C)=O)[CH:20]=2)[N:16]=[N:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CO>[CH2:7]([N:14]1[CH:18]=[C:17]([C:19]2[C:27]3[C:22](=[N:23][CH:24]=[C:25]([C:28]4[CH:29]=[N:30][N:31]([CH3:33])[CH:32]=4)[CH:26]=3)[NH:21][CH:20]=2)[N:16]=[N:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 66778317tert-butyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 497842883-(1-benzyl-1H-1,2,3-triazol-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.5 88 mg (0.63 mmol) of potassium carbonate are added to a solution of 115 mg (0.25 mmol) of tert-butyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate in 1.3 ml of methanol, and the mixture is stirred at room temperature for 1 hour. The reaction mixture is adsorbed onto kieselguhr and chromatographed on a silica-gel column with dichloromethane/methanol/ammonia water, giving 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine as colourless crystals; ESI 356;

Workup

  1. customchromatographed on a silica-gel column with dichloromethane/methanol/ammonia water

Sources & evidence

ORD record
ord-2bc2eca7ba31485e8558fa6fc5018c39
Source dataset
uspto-grants-2013_09
Patent number
US08541584B2

Linked notes

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