Triethylamine → HCID 86676324, compound
Reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1.[C:12](=[NH:25])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(N(CC)CC)C.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:19]1([C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N:25][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[N:4][CH:3]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1Participants
9
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 110 °C
Procedure
In a 250 mL round flask 4-bromoisoquinoline (1 g, 4.81 mmol), benzophenone imine (2.41 mL, 14.42 mL), Pd(OAc)2 (33 mg, 0.14 mmol), BINAP (299 mg, 0.05 mmol), DPPF (266 g, 0.05 mmol) and triethylamine (0.17 mL, 1.20 mmol) were concentrated in vacuum for 15 min and then dissolved in 50 mL anhydrous toluene at room temperature for 20 min. Cs2CO3 (2.35 g, 7.21 mmol) was added to the reaction mixture. The reaction mixture was heated at 110° C. for 18 h. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure to afford the crude which was purified by column chromatography to give N-(diphenylmethylene)-isoquinolin-4-amine (853 mg, 58%).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- filtrationfiltered
- concentrationThe filtrate was concentrated under reduced pressure
- customto afford the crude which
- customwas purified by column chromatography
Sources & evidence
- ORD record
- ord-b67cb7385d8e4a07a562fb828f0b970c
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029378B2
Reaction notes
Loading…