Methylamine → 4-Methylamino-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde
Reaction equation
Cl[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[N:10]([Si](C(C)C)(C(C)C)C(C)C)[CH:11]=[CH:12][C:3]=12.[CH3:23][NH2:24]>COC(O)C>[CH3:23][NH:24][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[NH:10][CH:11]=[CH:12][C:3]=12Participants
4
Conditions
- Temperature
- 120 °C
Procedure
A mixture of 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (5.9 g, 17.5 mmol), methyl amine (40 wt. % solution in water, 40 mL) in methoxyethanol (10 mL) is heated at 120° C. in a sealed tube. After overnight, the reaction mixture is cooled to room temperature and concentrated. The residue is dissolved in HCl solution (1N, 20 mL) and heated at 50° C. After stirring for 1.5 hours, the reaction mixture is basified with saturated sodium bicarbonate solution to pH=8. The solid is collected by filtration and washed with water, then hexanes, dried to afford the title compound as a solid. MS m/z 176.2 (M+1).
Workup
- temperaturethe reaction mixture is cooled to room temperature
- concentrationconcentrated
- dissolutionThe residue is dissolved in HCl solution (1N, 20 mL)
- temperatureheated at 50° C
- filtrationThe solid is collected by filtration
- washwashed with water
- dry with materialhexanes, dried
Sources & evidence
- ORD record
- ord-028fe40b487e425eb433f43f4e21c3c7
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07846923B2
Reaction notes
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