1,2-Dimethoxyethane → HCID 58407892, compound

HRID 414954Notes

Reaction equation

HRID 414954 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].[CH3:13][O:14][C:15]1[N:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.[F-].[Cs+].COCCOC>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(OCC)(=O)C.O>[CH3:12][O:11][C:9](=[O:10])[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:18]1[CH:19]=[N:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 25953Cesium fluorideHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 8063364Methyl 2-(2-bromophenyl)acetate

Product 1

HCID 58407892HCID 58407892, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
100 °C

Procedure

1.35 g (5.89 mmol) of methyl (2-bromophenyl)acetate are introduced together with 1 g (6.55 mmol) of 6-methoxypyridin-3-ylboronic acid and 1.98 g (13.09 mmol) of caesium fluoride into 20 ml of 1,2-dimethoxyethane under argon. After addition of 0.22 g (0.19 mmol) of tetrakis(triphenylphosphine)palladium(0), the reaction mixture is stirred at 100° C. for 4 h. Cooling to room temperature is followed by addition of a mixture of ethyl acetate and water and extraction with ethyl acetate. After the organic phase has been dried over magnesium sulphate and the solvent has been removed in vacuo, the residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 9:1). 1.1 g (68% of theory) of the product are obtained.

Workup

  1. temperatureCooling to room temperature
  2. dry with materialAfter the organic phase has been dried over magnesium sulphate
  3. customthe solvent has been removed in vacuo
  4. customthe residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 9:1)
  5. custom1.1 g (68% of theory) of the product are obtained

Sources & evidence

ORD record
ord-9e90a04db62c4cbcae7ca53c23be4751
Source dataset
uspto-grants-2012_01
Patent number
US08088769B2

Reaction notes

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