Triethylamine → 3-{[(6-Bromopyridin-2-yl)methyl]amino}cyclopent-2-en-1-one
Reaction equation
Cl.[Br:2][C:3]1[N:8]=[C:7]([CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:18]1(=O)[CH2:22][CH2:21][C:20](=[O:23])[CH2:19]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.[OH-].[Na+].[Cl-].[Na+].O>[Br:2][C:3]1[N:8]=[C:7]([CH2:9][NH:10][C:18]2[CH2:22][CH2:21][C:20](=[O:23])[CH:19]=2)[CH:6]=[CH:5][CH:4]=1Participants
9
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 95 °C
Procedure
A solution of 1-(6-bromopyridin-2-yl)methanamine hydrochloride (500 mg, 2.24 mmol) in toluene (10 ml) was charged with triethylamine (0.31 ml, 2.24 mmol). The reaction was stirred for 5 minutes after which cyclopentane-1,3-dione (330 mg, 3.36 mmol) and p-toluenesulfonic acid monohydrate (43 mg, 0.022 mmol) were added. The reaction mixture was heated to reflux at 95° C. for 45 minutes. The reaction mixture was cooled to ambient temperature and diluted with ethyl acetate (15 ml), 2N sodium hydroxide (10 ml) and brine (10 ml). The layers were separated and the organic layer was then dried over sodium sulfate, filtered and concentrated to yield the title compound.
Workup
- additionwere added
- temperatureThe reaction mixture was heated
- temperatureThe reaction mixture was cooled to ambient temperature
- customThe layers were separated
- dry with materialthe organic layer was then dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7685b9c3f3054c099daade80cd204f1a
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367706B2
Reaction notes
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