Potassium Carbonate → HCID 67126223, compound

HRID 514054Notes

Reaction equation

HRID 514054 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[CH2:10][CH:9]([CH3:19])[CH:8]=1)(=O)=O.[Cl:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.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.Cl[Pd]Cl.[Fe+2]>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[CH2:10][CH:9]([CH3:19])[CH:8]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 86691545HCID 86691545, compound

Product 1

HCID 67126223HCID 67126223, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 86587398Ethanol toluene waterSolvent

Conditions

Temperature
50 °C

Procedure

6-methoxy-3-methyl-3,4-dihydronaphthalen-1-yl trifluoromethanesulfonate (9.88 g, 30.7 mmol), 4-chlorophenylboronic acid (6.23 g, 39.9 mmol) and K2CO3 (12.7 g, 91.9 mmol) were combined in a mixture of toluene/ethanol/water (80 mL/40 mL/40 mL) at room temperature in a heavy walled pressure flask. Following sparging of the mixture with Ar for 30 minutes, PdCl2(dppf) (1.12 g, 1.53 mmol) was added in one portion and the flask was sealed and heated to 50° C. for 2.5 h. After returning to room temperature, the layers were separated and the aqueous layer was extracted with EtOAc and Hex (2×50 mL each). The combined organics were washed with brine, filtered through a pad of Celite, and dried over anhydrous MgSO4. The resulting solution was absorbed on silica gel in vacuo and purified via Yamazen column chromatography (0-15% EtOAc/Hex) to provide 7.7 g (88%) of the title compound as an amorphous white solid. 1H-NMR: 400 MHz, (CDCl3) δ: 7.32 (d, J=8 Hz, 2H); 7.26 (d, J=8 Hz, 2H); 6.87 (d, J=8.4 Hz, 1H); 6.57 (d, J=2.8 Hz, 1H); 6.62 (dd, J=8.4, 2.8 Hz, 1H); 5.74 (d, J=2.8 Hz, 1H); 3.79 (s, 3H); 2.81 (ABq, J=20.8, 12.4 Hz, 1H); 2.60 (m, 1H); 2.59 (ABq, J=8.4, 2.8 Hz, 1H); 1.14 (d, J=6.4 Hz, 3H).

Workup

  1. customFollowing sparging of the mixture with Ar for 30 minutes
  2. customthe flask was sealed
  3. customAfter returning to room temperature
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc and Hex (2×50 mL each)
  6. washThe combined organics were washed with brine
  7. filtrationfiltered through a pad of Celite
  8. dry with materialdried over anhydrous MgSO4
  9. customThe resulting solution was absorbed on silica gel in vacuo
  10. custompurified via Yamazen column chromatography (0-15% EtOAc/Hex)

Sources & evidence

ORD record
ord-b841788f57244f75996f036193119a28
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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