Formaldehyde → 3-(Dimethylaminomethyl)-7-azaindole
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.Cl.[CH3:11][NH:12][CH3:13].[CH2:14]=O>C(O)(C)C>[CH3:11][N:12]([CH3:14])[CH2:13][C:3]1[C:4]2[C:9](=[N:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
1H-Pyrrolo[2,3-b]pyridine (94, 5.0 g, 42 mmol), dimethylamine hydrochloride (3.8 g, 46 mmol), formaldehyde (1.4 g, 46 mmol) and isopropyl alcohol (220.0 mL) were combined in a pressure tube. The reaction mixture was stirred at 20° C. for 12 hours and then refluxed for 2 hours. The clear solution was evaporated to dryness in vacuo. Water (40 mL) and concentrated hydrochloric acid (4 mL) were added to the residue. The mixture was extracted with ether and then made strongly basic with potassium carbonate. The basified aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified by silica gel chromatography to give the compound (109, 5.0 g, 68%).
Workup
- temperaturerefluxed for 2 hours
- customThe clear solution was evaporated to dryness in vacuo
- additionWater (40 mL) and concentrated hydrochloric acid (4 mL) were added to the residue
- extractionThe mixture was extracted with ether
- extractionThe basified aqueous layer was extracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- custompurified by silica gel chromatography
- customto give the compound (109, 5.0 g, 68%)
Sources & evidence
- ORD record
- ord-c141ceee7bb24d5eb514f2dca003d770
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415469B2
Reaction notes
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