Potassium Hydroxide → (5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-[2-ethyl-5-(4-fluoro-benzylamino)-2H-pyrazol-3-yl]-methanone

HRID 1024310Notes

Reaction equation

HRID 1024310 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[OH-].[K+].[CH2:13]([N:15]1[C:19]([CH:20]=[O:21])=[CH:18][C:17]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[N:16]1)[CH3:14]>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:20]([C:19]3[N:15]([CH2:13][CH3:14])[N:16]=[C:17]([NH:22][CH2:23][C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[CH:18]=3)=[O:21])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 576192072-ethyl-5-(4-fluoro-benzylamino)-2H-pyrazole-3-carbaldehyde

Product 1

HCID 24954284(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-[2-ethyl-5-(4-fluoro-benzylamino)-2H-pyrazol-3-yl]-methanoneYield 2.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Chloro-1H-pyrrolo[2,3-b]pyridine (532, 0.068 g, 0.44 mmol) was combined with methanol (10 mL) and potassium hydroxide (0.16 g, 2.8 mmol). The mixture was stirred for 50 minutes, then 2-ethyl-5-(4-fluoro-benzylamino)-2H-pyrazole-3-carbaldehyde (530, 0.100 g, 0.40 mmol, prepared as described in Example 47, Scheme 162, Step 5) was added and the reaction was stirred overnight at room temperature and then concentrated. Ethyl acetate was added and the mixture was washed with sodium bicarbonate saturated solution and brine. After drying over anhydrous sodium sulfate the solvent was removed under reduced pressure. Purification with silica gel column chromatography eluting with a gradient of ethyl acetate (10-100%) in hexanes provided the desired compound (0.0033 g, 2%). MS (ESI) [M+H+]+=398.1.

Workup

  1. stirringthe reaction was stirred overnight at room temperature
  2. concentrationconcentrated
  3. additionEthyl acetate was added
  4. washthe mixture was washed with sodium bicarbonate saturated solution and brine
  5. dry with materialAfter drying over anhydrous sodium sulfate the solvent
  6. customwas removed under reduced pressure
  7. customPurification with silica gel column chromatography
  8. washeluting with a gradient of ethyl acetate (10-100%) in hexanes

Sources & evidence

ORD record
ord-f1becfd1c34142279c80c9bfe2f184ef
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

Loading…