Potassium Carbonate → Ethyl acetate hexane
Reaction equation
BrC1NC(=O)C2C(C=1)=C[C:8]([O:12]C)=[C:7](OC)C=2.[C:17]1([C:26]2[CH:31]=CC=CC=2)[CH:22]=[CH:21][CH:20]=[C:19](B(O)O)[CH:18]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=[O:67].[K+].[K+]>CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:7][CH2:8][O:12][C:26]([CH3:31])=[O:67].[CH3:21][CH2:22][CH2:17][CH2:18][CH2:19][CH3:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
3-Bromo-6,7-dimethoxyisoquinolin-1(2H)-one (550 mg) was combined with 3-biphenyl boronic acid (768 mg, 2 eq.), Pd(OAc)2 (43.5 mg, 0.1 eq.), XPhos (185 mg, 0.2 eq.), and K2CO3 (1.07 g, 4 eq.) in a flask and degassed. 15 mL ACN and 7.5 mL of H2O were then added and solution was heated at 100° C. for 1.5 hours. Reaction mixture was cooled to room temperature then diluted with EtOAc and washed with NaHCO3. Organic layer was dried over sodium sulfate and concentrated. Chromatography achieved using ISCO max gradient 70% EtOAc/hexane yielding product as a white solid (540 mg, 78% yield). 1H NMR (400 MHz) (CDCl3) δ 9.98 (s, 1H), 7.97 (m, 1H), 7.78 (s, 1H), 7.75-7.67 (m, 4H), 7.60 (t, J=16 Hz, 1H), 7.50-7.46 (m, 2H), 7.43-7.39 (m, 1H), 7.01 (s, 1H), 6.81 (s, 1H), 4.05 (s, 3H), 3.96 (s, 3H). 13C NMR (100 MHz) (CDCl3) δ 163.48, 153.93, 149.28, 142.03, 140.35, 138.47, 135.10, 133.92, 129.54, 128.93, 127.81, 127.75, 127.17, 125.07, 124.97, 118.99, 107.38, 106.57, 104.19, 56.11, 56.09. MP: 229-231° C.
Workup
- customdegassed
- addition15 mL ACN and 7.5 mL of H2O were then added
- customReaction mixture
- temperaturewas cooled to room temperature
- washwashed with NaHCO3
- dry with materialOrganic layer was dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-da11ebde2423496b96d6487ec9765bf5
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933096B2
Reaction notes
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