Methanol → 1-ethyl-5-[methoxy-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-1H-pyrazol-3-yl-(4-fluoro-benzyl)-amine
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
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
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated
- custompurified by silica gel column chromatography
- washeluting with 40% ethyl acetate in hexane
- customto give a white solid (531, 0.12 g, 71.1%)
Sources & evidence
- ORD record
- ord-cb5a56369fbd412c966488bb9d3d598a
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09169250B2
Reaction notes
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