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 concentratred 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 methylene chloride, dried over sodium sulfate and concentrated to give product, which was then further washed with ether and dried to afford the product 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 methylene chloride
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customto give product, which
- washwas then further washed with ether
- customdried
Sources & evidence
- ORD record
- ord-c678e63368ab4cf7bc500a3f9f2690e3
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07498342B2
Reaction notes
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