Methanol → 3-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)(methoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1754699Notes

Reaction equation

HRID 1754699 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[Cl:10][C:11]1[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:14]=[C:13]([CH3:22])[C:12]=1[CH:23]=[O:24].[OH-].[K+].[CH3:27]O>>[Cl:10][C:11]1[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:14]=[C:13]([CH3:22])[C:12]=1[CH:23]([O:24][CH3:27])[C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:1][CH:2]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14797Potassium HydroxideHCID 6130275-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 595933583-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)(methoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

Procedure

To 1H-Pyrrolo[2,3-b]pyridine (1, 0.100 g, 0.846 mmol) and 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (100, 0.205 g, 0.931 mmol) was added 2 mL of methanol to give a solution. Potassium hydroxide (0.0475 g, 0.846 mmol) was added and the reaction was allowed to stir at room temperature for 48 hours. The reaction was extracted with ethyl acetate and water. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with a gradient of 0-5% methanol in dichloromethane to give the compound (P-0079, 32 mg, 11%). MS (ESI) [M+H+]+=353.2.

Workup

  1. customto give a solution
  2. extractionThe reaction was extracted with ethyl acetate and water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography
  7. washeluting with a gradient of 0-5% methanol in dichloromethane
  8. customto give the compound (P-0079, 32 mg, 11%)

Sources & evidence

ORD record
ord-45e7629661fa41c2bbe3c49be46aa8bb
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

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