Hexamethylenetetramine → 4-fluoro-1-(3-methoxypropyl)-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:9]=[CH:10][C:3]=12.C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:28](O)=[O:29]>>[F:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:9]=[C:10]([CH:28]=[O:29])[C:3]=12Participants
4
Procedure
A solution of 4-fluoro-1-(3-methoxypropyl)-1H-pyrrolo[2,3-b]pyridine (520 mg) and hexamethylenetetramine (700 mg) in trifluoroacetic acid (9.1 ml) was stirred at 80° C. for 4 hours. After evaporation of the solvent in vacuo, the resulted residue was dissolve in ethyl acetate. The solution was poured slowly into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=60/40 to 20/80) to give 4-fluoro-1-(3-methoxypropyl)-1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde (260 mg) as a colorless oil.
Workup
- customAfter evaporation of the solvent in vacuo
- dissolutionthe resulted residue was dissolve in ethyl acetate
- additionThe solution was poured slowly into a saturated aqueous solution of sodium bicarbonate
- extractionextracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=60/40 to 20/80)
Sources & evidence
- ORD record
- ord-ba5ca38261e04879b00715588723f4db
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975252B2
Reaction notes
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