Dimethylformamide → 1-Benzyl-6-chloro-2-isopropyl-1H-pyrrolo[3,2-c]pyridine-3-carbaldehyde
Reaction equation
O=P(Cl)(Cl)Cl.[CH2:6]([N:13]1[C:21]2[CH:20]=[C:19]([Cl:22])[N:18]=[CH:17][C:16]=2[CH:15]=[C:14]1[CH:23]([CH3:25])[CH3:24])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CN([CH:29]=[O:30])C>>[CH2:6]([N:13]1[C:21]2[CH:20]=[C:19]([Cl:22])[N:18]=[CH:17][C:16]=2[C:15]([CH:29]=[O:30])=[C:14]1[CH:23]([CH3:25])[CH3:24])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1Participants
4
Conditions
- Temperature
- 80 °C
Procedure
POCl3 (0.31 ml, 3.42 mmol) was added to anhydrous DMF (5 ml) at 0° C. slowly and stirred for 20 min. To this solution was added a solution of 1-benzyl-6-chloro-2-isopropyl-1H-pyrrolo[3,2-c]pyridine (Compound 13, 195 mg, 0.68 mmol) in anhydrous DMF (7 ml) at room temperature. The mixture was stirred at room temperature for 2 h and was then heated to 60° C. for 2 h and 80° C. for 0.5 h. The reaction was cooled to room temperature, quenched cautiously with aqueous Na2CO3, extracted with EtOAc (×2). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes) to yield the title compound.
Workup
- stirringThe mixture was stirred at room temperature for 2 h
- temperatureThe reaction was cooled to room temperature
- customquenched cautiously with aqueous Na2CO3
- extractionextracted with EtOAc (×2)
- washThe combined organic layer was washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes)
Sources & evidence
- ORD record
- ord-c975c3e6da9d481e995b9e2b207387d9
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08012992B2
Reaction notes
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