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

HRID 45581Notes

Reaction equation

HRID 45581 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]3[C:15]([C:16]4[N:17]=[N:18][N:19]([CH:21]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH3:22])[CH:20]=4)=[CH:14][N:13](C(OC(C)(C)C)=O)[C:10]3=[N:11][CH:12]=2)[CH:4]=[N:3]1.C(=O)([O-])[O-].[K+].[K+].O>CO>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]3[C:15]([C:16]4[N:17]=[N:18][N:19]([CH:21]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH3:22])[CH:20]=4)=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 66779091tert-Butyl 5-(1-methyl-1H-pyrazol-4-yl)-3-[1-(1-phenylethyl)-1H-1,2,3-triazol-4-yl]pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 497842925-(1-methyl-1H-pyrazol-4-yl)-3-[1-(1-phenylethyl)-1H-1,2,3-triazol-4-yl]-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 5-(1-methyl-1H-pyrazol-4-yl)-3-[1-(1-phenylethyl)-1H-1,2,3-triazol-4-yl]pyrrolo[2,3-b]pyridine-1-carboxylate (90 mg, 0.176 mmol) is dissolved in MeOH (5 ml), potassium carbonate (85 mg, 0.615 mmol) is added, and the mixture is stirred at RT for 1 h. Water is added, and the mixture is extracted three times with ethyl acetate. The organic phase is washed with saturated NaCl solution, dried over Na2SO4 and evaporated to dryness. The residue is triturated with ether and filtered off with suction, washed with ether and dried in a high vacuum, giving 5-(1-methyl-1H-pyrazol-4-yl)-3-[1-(1-phenylethyl)-1H-1,2,3-triazol-4-yl]-1H-pyrrolo[2,3-b]pyridine as colourless solid; HPLC/MS: Rt=1.874 min, [M+H]+ 370;

Workup

  1. extractionthe mixture is extracted three times with ethyl acetate
  2. washThe organic phase is washed with saturated NaCl solution
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customThe residue is triturated with ether
  6. filtrationfiltered off with suction
  7. washwashed with ether
  8. customdried in a high vacuum

Sources & evidence

ORD record
ord-7b86e44dafde4b1a8ffe1afb068cf285
Source dataset
uspto-grants-2013_09
Patent number
US08541584B2

Reaction notes

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