Potassium Carbonate → Ethyl acetate hexane
Reaction equation
FC(F)(F)S([O:6][C:7]1C=CC=C(C2N=C(C)C3C(C=2)=CC(OC)=C(OC)C=3)[CH:8]=1)(=O)=O.[C:30]([C:34]1[CH:39]=C[C:37](B(O)O)=[CH:36][CH:35]=1)(C)(C)[CH3:31].C([O-])([O-])=[O:44].[K+].[K+]>C(#N)C.O.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>[CH3:8][CH2:7][O:6][C:34]([CH3:39])=[O:44].[CH3:31][CH2:30][CH2:34][CH2:35][CH2:36][CH3:37]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 5
Conditions
- Temperature
- 95 °C
Procedure
3-(6,7-Dimethoxy-1-methylisoquinolin-3-yl)phenyl trifluoromethanesulfonate (130 mg), 4-t-butylphenylboronic acid (108 mg, 2 eq.), Pd(OAc)2 (7 mg, 0.1 eq.), XPhos (29 mg, 0.2 eq.), and K2CO3 (147 mg, 3.5 eq.) in 3 mL ACN and 1.5 mL H2O were combined in a flask and degassed. Reaction mixture was heated to 95° C. for 2 hours. Solution was then cooled to room temperature, diluted with EtOAc, and washed with saturated NaHCO3. Organic layer was dried over sodium sulfate and concentrated. Chromatography achieved using ISCO max gradient 40% EtOAc/hexane yielding product as a white solid (121 mg, 97% yield). 1H NMR (400 MHz) (CDCl3) δ 8.35-8.34 (m, 1H), 8.08 (d, J=8 Hz, 1H), 7.88 (s, 1H), 7.68 (d, J=8 Hz, 2H), 7.63 (d, J=8 Hz, 1H), 7.56 (t, J=16 Hz, 1H), 7.53 (d, J=8 Hz, 2H), 7.33 (s, 1H), 7.16 (s, 1H), 4.09 (s, 3H), 4.08 (s, 3H), 3.00 (s, 3H), 1.41 (s, 9H). 13C NMR (100 MHz) (CDCl3) δ 155.95, 152.67, 150.26, 149.84, 149.25, 141.47, 140.63, 138.58, 133.47, 129.01, 126.95, 126.71, 125.69, 125.65, 125.53, 122.32, 114.47, 105.72, 103.97, 56.02, 34.55, 31.40, 22.74.
Workup
- customdegassed
- customReaction mixture
- temperatureSolution was then cooled to room temperature
- washwashed with saturated NaHCO3
- dry with materialOrganic layer was dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e0f350c4447d4aeab2faabedfab1e723
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933096B2
Reaction notes
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