Potassium Carbonate → Ethyl acetate hexane

HRID 1426264Notes

Reaction equation

HRID 1426264 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.C(C1C=C(B(O)O)C=[CH:32][CH:33]=1)(C)(C)C.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=[O:72].[K+].[K+]>CCOC(C)=O.O.O1CCOCC1>[CH3:16][CH2:7][O:6][C:32]([CH3:33])=[O:72].[CH3:21][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 21582509(3-tert-Butylphenyl)boronic acidHCID 59322850HCID 59322850, compound

Product 1

HCID 21226206Ethyl acetate hexaneYield 164.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

6,7-Dimethoxy-1-methylisoquinolin-3-yl trifluoromethanesulfonate (300 mg), 3-t-butylphenylboronic acid (183 mg, 1.2 eq.), Pd(OAc)z (19 mg, 0.1 eq.), XPhos (81 mg, 0.2 eq.), and K2CO3 (354 mg, 3 eq.) were combined in a flask with 9 mL dioxane and 3 mL H2O and degassed. Reaction mixture was then refluxed at 100° C. for 2 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 40% EtOAc/hexane yielding product as a clear oil (245 mg, 83% yield). 1H NMR (400 MHz) (CDCl3) δ 8.14 (s, 1H), 7.92-7.89 (m, 1H), 7.81 (s, 1H), 7.45-7.44 (m, 2H), 7.31 (s, 1H), 7.15 (s, H), 4.08 (s, 3H), 4.07 (s, 3H), 3.00 (s, 3H), 1.44 (s, 9H). 13C NMR (100 MHz) (CDCl3) δ 155.86, 152.59, 151.39, 149.88, 149.70, 139.95, 133.48, 128.37, 125.13, 124.16, 123.88, 122.16, 114.45, 105.67, 103.92, 56.03, 55.99, 34.88, 31.48, 22.79.

Workup

  1. customdegassed
  2. customReaction mixture
  3. temperatureSolution was cooled to room temperature
  4. washwashed with saturated NaHCO3
  5. dry with materialOrganic layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b3eb3ce821804b6399d24f88f1888cb0
Source dataset
uspto-grants-2015_01
Patent number
US08933096B2

Reaction notes

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