Ethyl Acrylate → HCID 68706213, compound

HRID 2069312Notes

Reaction equation

HRID 2069312 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.P.[CH2:16]([O:18][C:19](=[O:22])[CH:20]=[CH2:21])[CH3:17]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[CH2:16]([O:18][C:19](=[O:22])[CH:20]=[CH:21][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1)[CH3:17]

Participants

6

Reactant 3

HCID 8821Ethyl AcrylateHCID 24404PhosphineHCID 221807795-Bromo-2-(4-fluorophenyl)pyridine

Product 1

HCID 68706213HCID 68706213, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

9.30 g (36.9 mmol) of 5-bromo-2-(4-fluoro-phenyl)-pyridine were mixed with 100 ml of triethylamine, 2.06 g (9.2 mmol) of palladium acetate, 2.80 g (9.2 mmol) of tri)ortho-tolyl)phosphine and 6.47 g (64.6 mmol) of acrylic acid ethyl ester and heated to 90° C. for 2 h. The reaction mixture was evaporated, taken up in water and extracted with ethyl acetate. The combined organic phases were dried and evaporated, and the residue was subjected to column chromatography (silica gel, n-heptane/ethyl acetate 3:1). Yield: 7.7 g.

Workup

  1. customThe reaction mixture was evaporated
  2. extractionextracted with ethyl acetate
  3. customThe combined organic phases were dried
  4. customevaporated

Sources & evidence

ORD record
ord-d159d3ba97454be6a663c475ee9ec488
Source dataset
uspto-grants-2012_10
Patent number
US08299102B2

Reaction notes

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