Potassium Carbonate → HCID 58892518, compound
Reaction equation
B([O-])([O-])O[C:3]1[CH:8]=C[CH:6]=[C:5]([CH3:9])[CH:4]=1.Cl[C:13]1[CH:22]=[C:21]([CH3:23])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.[C:24](=O)([O-])[O-].[K+].[K+]>C1COCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:9][C:5]1[CH:6]=[C:16]([C:15]2[C:20]3[C:21](=[CH:23][CH:17]=[CH:18][CH:19]=3)[C:22]([CH3:24])=[CH:13][N:14]=2)[CH:8]=[CH:3][CH:4]=1Participants
7
Conditions
- Temperature
- 100 °C
Procedure
3-Methylphenyl borate (1.3 mmol), 2-chloro-4-methylquinoline (1 mmol), tetrakis(triphenylphosphine) palladium(0) (0.05 mmol) and potassium carbonate (3 mmol) were dissolved in THF (30 mL) and H2O (10 mL). The resulting solution was stirred in a bath at 100° C. for 24 hours. After completion of the reaction, the solvents were removed. The reaction mixture was extracted with dichloromethane and water and distilled under reduced pressure. The resulting residue was purified by silica gel column chromatography. The eluate was distilled under reduced pressure. The residue was recrystallized from dichloromethane and petroleum ether, and filtered to yield 1-(3-methylphenyl)-4-methylisoquinoline as a solid.
Workup
- customAfter completion of the reaction
- customthe solvents were removed
- extractionThe reaction mixture was extracted with dichloromethane and water
- distillationdistilled under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography
- distillationThe eluate was distilled under reduced pressure
- customThe residue was recrystallized from dichloromethane and petroleum ether
- filtrationfiltered
Sources & evidence
- ORD record
- ord-66af5de44e80428d975c7c8d950fc2f8
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501328B2
Reaction notes
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