Sodium Carbonate → HCID 66632989, compound

HRID 1961423Notes

Reaction equation

HRID 1961423 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[O:14]1[CH2:19][CH:18]=[C:17](B2OC(C)(C)C(C)(C)O2)[CH2:16][CH2:15]1.C([O-])([O-])=O.[Na+].[Na+].[Li+].[Cl-]>C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[O:14]1[CH2:15][CH:16]=[C:17]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[C:10]([F:13])([F:12])[F:11])[CH2:18][CH2:19]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 1442554-Fluoro-3-(trifluoromethyl)benzonitrileHCID 433294Lithium ChlorideHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol ester

Product 1

HCID 66632989HCID 66632989, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

In a screw cap pressure tube, 4-fluoro-3-(trifluoromethyl)-benzonitrile (425 mg, 1.70 mmol) and 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (357.1 mg, 1.70 mmol) were dissolved in dimethoxyethane. Na2CO3 (2 M aq. sln, 2.5 ml) and LiCl (216.4 mg, 5.1 mmol) were added. N2 was bubbled through the mixture for 5 minutes. Pd(PPh3)4 (39.3 mg, 0.03 mmol) was added. The tube was sealed and the mixture heated to reflux for 20 h. The mixture was allowed to cool. H2O was added and the product extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography; Pet. Ether, EtOAc (4:1) affording 254 mg (59%) the title compound.

Workup

  1. customIn a screw cap pressure tube
  2. customN2 was bubbled through the mixture for 5 minutes
  3. customThe tube was sealed
  4. temperaturethe mixture heated
  5. temperatureto reflux for 20 h
  6. temperatureto cool
  7. extractionthe product extracted with EtOAc
  8. dry with materialThe combined organic extracts were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-2597e71b042a4667905f493c2be55a7e
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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