Sodium Carbonate → HCID 86718610, compound

HRID 1480644Notes

Reaction equation

HRID 1480644 reaction equation
Br[C:2]1[C:3]([O:14][CH2:15][O:16][CH3:17])=[C:4]([CH:7]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:9]=1)[CH:5]=[O:6].[F:18][C:19]([F:30])([F:29])[C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][N:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>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>[C:10]([C:8]1[CH:9]=[C:2]([C:23]2[CH:22]=[N:21][C:20]([C:19]([F:30])([F:29])[F:18])=[CH:25][CH:24]=2)[C:3]([O:14][CH2:15][O:16][CH3:17])=[C:4]([CH:7]=1)[CH:5]=[O:6])([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 251342782-(Trifluoromethyl)pyridine-5-boronic AcidHCID 86718609HCID 86718609, compound

Product 1

HCID 86718610HCID 86718610, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a degassed (argon) solution of 3-bromo-5-(tert-butyl)-2-(methoxymethoxy)benzaldehyde (4.0 g, 13.3 mmol) and 2-(trifluoromethyl)pyridine-5-boronic acid [purchased from Frontier Scientific] (2.79 g, 14.6 mmol) in 2M aqueous sodium carbonate solution (26.7 mL, 53.2 mmol) and dimethoxy ethane (80 mL) was added tetrakis(triphenylphosphine)palladium(0) (770 mg, 0.665 mmol), the mixture was degassed for five minutes and then heated at 80° C. for 16 hours. The cooled reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic phase was separated, dried (Na2SO4), filtered and concentrated under reduced pressure to give an orange syrup. The product was purified using flash chromatography on silica eluting with a solvent gradient of 0 to 100% ethyl acetate in hexanes to give the 5-(tert-butyl)-2-(methoxymethoxy)-3-(6-(trifluoromethyl)pyridin-3-yl)benzaldehyde (3.7 g, 76% yield) as a grey-green solid.

Workup

  1. customthe mixture was degassed for five minutes
  2. customThe cooled reaction mixture
  3. customwas partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  4. customThe organic phase was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give an orange syrup
  9. customThe product was purified

Sources & evidence

ORD record
ord-9fd35bb123ab4d1caacde3a211c2d709
Source dataset
uspto-grants-2016_08
Patent number
US09409893B2

Reaction notes

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