Potassium Carbonate → Ethyl acetate hexane
Reaction equation
FC(F)(F)S([O:6][C:7]1N=[C:9]([CH3:21])[C:10]2C([CH:16]=1)=C[C:13](OC)=[C:12](OC)[CH:11]=2)(=O)=O.C1([C:33]2[CH:38]=CC=CC=2)C=CC=C(B(O)O)C=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:74].[K+].[K+]>CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].O.C(#N)C>[CH3:16][CH2:7][O:6][C:33]([CH3:38])=[O:74].[CH3:21][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 100 °C
Procedure
6,7-Dimethoxy-1-methylisoquinolin-3-yl trifluoromethanesulfonate (575 mg), 3-biphenylboronic acid (390 mg, 1.2 eq.), Pd(OAc)2 (37 mg, 0.1 eq.), XPhos (156 mg, 0.2 eq.), and K2CO3 (792 mg, 3.5 eq.) were combined in a flask with 9 mL ACN and 3 mL H2O and degassed. Reaction mixture was then refluxed at 100° C. for 5 hours. Solution was cooled to room temperature then diluted with EtOAc and washed with saturated NaHCO3. Organic layer was dried over sodium sulfate and concentrated. Chromatography achieved using ISCO max gradient 30% EtOAc/hexane yielding product as white solid (473 mg, 81% yield). 1H NMR (400 MHz) (CDCl3) δ 8.36 (m, 1H), 8.11-8.09 (m, 1H), 7.89 (s, 1H), 7.75-7.73 (m, 2H), 7.64-7.62 (m, 1H), 7.58 (t, J=12 Hz, 2H), 7.50 (t, J=16 Hz, 1H), 7.40 (t, J=12 Hz, 1H), 7.33 (s, 1H), 7.16 (s, 1H), 4.09 (s, 3H), 4.08 (s, 3H), 3.01 (s, 3H). 13C NMR (100 MHz) (CDCl3) δ 155.99, 152.69, 149.87, 149.15, 141.64, 141.49, 140.71, 133.47, 129.08, 128.70, 127.33, 127.25, 126.83, 125.77, 122.35, 114.51, 105.72, 103.96, 56.02, 22.76.
Workup
- customdegassed
- customReaction mixture
- temperatureSolution was cooled to room temperature
- washwashed with saturated NaHCO3
- dry with materialOrganic layer was dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6adb499401c64f40b8f2c4174431fdb7
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933096B2
Reaction notes
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