Acetonitrile → HCID 59455235, compound
Reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([C:15]([O-])=O)[CH2:14][C:5]=3[C:4]=2[CH:3]=1.Br[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.C(N([CH2:30][CH3:31])CC)C.[C:32](#N)C>[Cu]I>[CH3:15][N:13]1[CH2:12][CH2:11][C:6]2[N:7]([CH2:32][C:30]#[C:31][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[C:8]3[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][C:4]=3[C:5]=2[CH2:14]1Participants
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 2,3,4,5-tetrahydro-2,8-dimethyl-5-(prop-2-ynyl)-1H-pyrido[4,3-b]indole (obtained by General Method 8; p-tolylhydrazine hydrochloride (600 mg, 3.7 mmol), propargyl bromide (80 wt % solution in toluene, 0.34 ml, 3.7 mmol), triethyl amine (1.5 ml, 11.3 mmol) and N-methyl-4-piperidone hydrochloride (316 mg, 2.1 mmol) were taken in ethanol (15 ml) to obtain 80 mg of 2,3,4,5-tetrahydro-2,8-dimethyl-5-(prop-2-ynyl)-1H-pyrido[4,3-b]indole after purification on silica gel (230-400 mesh) chromatography eluting with methanol-dichloromethane gradient) (150 mg, 0.6 mmol), 2-bromopyridine (0.06 ml, 0.6 mmol), dichlorobis(triphenylphosphine) palladium (8 mg, 0.012 mmol), CuI (1 mg, 0.006 mmol), and triethylamine (0.01 ml 0.07 mmol) in acetonitrile (5 ml) was heated at 80° C. for 1.5 h to obtain 108 mg of 2,3,4,5-tetrahydro-2,8-dimethyl-5-(3-(pyridin-2-yl)prop-2-ynyl)-1H-pyrido[4,3-b]indole after purification by reverse-phase chromatography (C-18, 500 mm×50 mm, Mobile Phase A=0.05% TFA in water, B=0.05% TFA in acetonitrile, Gradient: 10% B to 80% B in 30 min, injection vol. 5 mL).
Sources & evidence
- ORD record
- ord-5b87a32d4ddb45dc90e949b374d94ec8
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999978B2
Reaction notes
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