Methanol → 1-ethyl-5-[methoxy-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-1H-pyrazol-3-yl-(4-fluoro-benzyl)-amine

HRID 1367351Notes

Reaction equation

HRID 1367351 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[CH2:10]([N:12]1[C:16]([CH:17]=[O:18])=[CH:15][C:14]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[N:13]1)[CH3:11].[OH-].[K+].O.[CH3:31]O>>[CH2:10]([N:12]1[C:16]([CH:17]([O:18][CH3:31])[C:3]2[C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:1][CH:2]=2)=[CH:15][C:14]([NH:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)=[N:13]1)[CH3:11]

Participants

6

Reactant 5

HCID 887MethanolHCID 962WaterHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14797Potassium HydroxideHCID 576192072-ethyl-5-(4-fluoro-benzylamino)-2H-pyrazole-3-carbaldehyde

Product 1

HCID 576194351-ethyl-5-[methoxy-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-1H-pyrazol-3-yl-(4-fluoro-benzyl)-amine

Procedure

To 1H-Pyrrolo[2,3-b]pyridine (1, 54.0 mg, 0.46 mmol) in methanol (15.0 mL) were added 2-ethyl-5-(4-fluoro-benzylamino)-2H-pyrazole-3-carbaldehyde (530, 110.0 mg, 0.44 mmol) and potassium hydroxide (0.60 g, 0.011 mol) under an atmosphere of nitrogen. The reaction was stirred at room temperature overnight, then 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 40% ethyl acetate in hexane to give a white solid (531, 0.12 g, 71.1%). MS (ESI) [M−H+]−=378.2.

Workup

  1. extraction(extracted 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 40% ethyl acetate in hexane
  7. customto give a white solid (531, 0.12 g, 71.1%)

Sources & evidence

ORD record
ord-bce8f4bf6129476288b12dadb526af01
Source dataset
uspto-grants-2011_02
Patent number
US07893075B2

Reaction notes

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