Water → [2,6-dichloro-3-(2,2,2-trifluoro-ethoxy)-phenyl]-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-methanol

HRID 253435Notes

Reaction equation

HRID 253435 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]3[CH:15]=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH:4]=[N:3]1.[Cl:16][C:17]1[C:24]([O:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=[C:21]([Cl:31])[C:18]=1[CH:19]=[O:20].[OH-].[K+].O>CO>[Cl:16][C:17]1[C:24]([O:25][CH2:26][C:27]([F:29])([F:30])[F:28])=[CH:23][CH:22]=[C:21]([Cl:31])[C:18]=1[CH:19]([C:15]1[C:9]2[C:10](=[N:11][CH:12]=[C:7]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)[CH:8]=2)[NH:13][CH:14]=1)[OH:20]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 580861115-(1-Methyl-1H-pyrazol-4-YL)-1H-pyrrolo[2,3-B]pyridineHCID 598038422,6-Dichloro-3-(2,2,2-trifluoro-ethoxy)-benzaldehyde

Product 1

HCID 59803863[2,6-dichloro-3-(2,2,2-trifluoro-ethoxy)-phenyl]-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-methanolYield 75.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine (109, 100.0 mg, 0.51 mmol, prepared as described in Example 35) in methanol (30 mL) were added 2,6-dichloro-3-(2,2,2-trifluoro-ethoxy)-benzaldehyde (115, 154 mg, 0.56 mmol) and potassium hydroxide (596.0 mg, 10.62 mmol) under an atmosphere of nitrogen. The reaction was stirred at room temperature overnight. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 2% to 25% methanol in dichloromethane to give the desired compound (116, 0.18 g, 75.7%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 2% to 25% methanol in dichloromethane

Sources & evidence

ORD record
ord-2e79faeec93540139592cd736dbb7594
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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