Hydrochloric Acid → 3-(Dimethylaminomethyl)-7-azaindole
Reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.Cl.[CH3:11][NH:12][CH3:13].[CH2:14]=O.O.Cl>C(O)(C)C>[CH3:11][N:12]([CH3:14])[CH2:13][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:1][CH:2]=1Participants
Procedure
Into a 3-neck round bottom flask was added Isopropyl alcohol (320.0 mL) followed by the addition of 1H-pyrrolo[2,3-b]pyridine 1 (7.10 g, 60.1 mmol), dimethylamine hydrochloride (5.4 g, 0.066 mol), and formaldehyde (2.0 g, 0.066 mol). The reaction mixture was stirred at room temperature for 12 hours, and then refluxed for 30 minutes. The suspension solution was evaporated to dryness in vacuo. To the residue was added water (60.0 mL, 3.33 mol) and concentrated hydrochloric acid (6.0 mL, 0.20 mol). The water layer was extracted with ether and the aqueous layer was neutralized with potassium carbonate. The aqueous layer was extracted with dichloromethane, dried over sodium sulfate and concentrated to give the compound, which was then further washed with ether and dried to afford compound 2 (7.1 g, yield=67.4%), as a white solid.
Workup
- temperaturerefluxed for 30 minutes
- customThe suspension solution was evaporated to dryness in vacuo
- extractionThe water layer was extracted with ether
- extractionThe aqueous layer was extracted with dichloromethane
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customto give the compound, which
- washwas then further washed with ether
- customdried
Sources & evidence
- ORD record
- ord-997f1958ca0d4941a0343033ed50c94c
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722702B2
Reaction notes
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