Methyl Acrylate → HCID 69653027, compound

HRID 1369926Notes

Reaction equation

HRID 1369926 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH2:15][CH2:14][CH2:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1.[CH3:16][O:17][C:18](=[O:21])[CH:19]=[CH2:20].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.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>[CH3:16][O:17][C:18]([CH:19]=[CH:20][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH2:15][CH2:14][CH2:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1)=[O:21]

Participants

7

Reactant 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 15429321HCID 15429321, compound

Product 1

HCID 69653027HCID 69653027, compoundYield 102.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 528 mg (2.0 mmol) of 7-bromo-1,2,3,5-tetrahydrocyclopenta[c]quinolin-4-one (WO 99/41240), 0.36 ml (4.0 mmol) of acrylic acid methyl ester, 116 mg (0.1 mmol) of tetrakis(triphenylphosphine)palladium and 0.56 ml (4.0 mmol) of triethylamine in 25 ml of DMF is stirred for 3 hours at 120° C. The batch is diluted with ethyl acetate, washed with water, dried (Na2SO4) and concentrated by evaporation in a vacuum. Purification of the residue on silica gel with dichloromethane-ethanol yields 550 mg of product.

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated by evaporation in a vacuum
  4. customPurification of the residue on silica gel with dichloromethane-ethanol

Sources & evidence

ORD record
ord-8d357a14b7af42b5bae3fbceef322481
Source dataset
uspto-grants-2003_06
Patent number
US06579883B1

Reaction notes

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