Water → HCID 32639806, compound
Reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([C:10]1[NH:18][C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[CH:11]=1)([CH3:9])([CH3:8])[CH3:7].O.[OH-].[Na+].CN(C)[CH:24]=[O:25]>>[C:6]([C:10]1[NH:18][C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[C:11]=1[CH:24]=[O:25])([CH3:9])([CH3:7])[CH3:8]Participants
Procedure
Phosphorous oxychloride (4.01 mL, 43 mmol) was added drop-wise to N,N-dimethylformamide (9.96 mL, 129 mmol) at 0° C. and the mixture was stirred for 20 min. A solution of 2-tert-butyl-1H-pyrrolo[2,3-b]pyridine (5.0 g, 28.7 mmol) dissolved in N,N-dimethylformamide (30 mL) was added and the resulting mixture was slowly warmed up to room temperature. The mixture was stirred at room temperature for 2 h then at 40° C. for 3 h, and cooled in an ice bath, and 0.5 mL water was added. The reaction mixture was slowly warmed to 40° C. and stirred for 20 h. The mixture was poured onto approximately 100 mL ice, neutralized with an aqueous sodium hydroxide (5%) and extracted with dichloromethane. The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo, and the residue was purified via silica gel column chromatography (0-30% ethyl acetate in heptane) to obtain 2-tert-butyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (2.4 g, 11.9 mmol, 41% yield) as an off white solid.
Workup
- additionwas added
- stirringThe mixture was stirred at room temperature for 2 h
- waitat 40° C. for 3 h
- temperaturecooled in an ice bath
- temperatureThe reaction mixture was slowly warmed to 40° C.
- stirringstirred for 20 h
- extractionextracted with dichloromethane
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customthe residue was purified via silica gel column chromatography (0-30% ethyl acetate in heptane)
Sources & evidence
- ORD record
- ord-9d040fdfc83a4fffb71381861cf1b2be
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07943652B2
Reaction notes
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