Methyl Acrylate → HCID 10210567, compound

HRID 488881Notes

Reaction equation

HRID 488881 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([Cl:19])=[C:15]([CH3:18])[CH:16]=3)[O:11][C:10](=[O:20])[C:9]=2[CH2:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[C:32]([F:35])([F:34])[F:33])=[O:23])[CH:5]=[CH:6][CH:7]=1.[C:36]([O:40][CH3:41])(=[O:39])[CH:37]=[CH2:38].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.CC(O)=O.CC(O)=O.[Pd].O>[Cl:19][C:14]1[CH:13]=[C:12]2[C:17]([C:8]([C:4]3[CH:3]=[C:2](/[CH:38]=[CH:37]/[C:36]([O:40][CH3:41])=[O:39])[CH:7]=[CH:6][CH:5]=3)=[C:9]([CH2:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=3[C:32]([F:34])([F:35])[F:33])=[O:23])[C:10](=[O:20])[O:11]2)=[CH:16][C:15]=1[CH3:18]

Participants

8

Reactant 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 22267230HCID 22267230, compound

Product 1

HCID 10210567HCID 10210567, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 4144353Palladium (II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 2-[4-(3-bromophenyl)-7-chloro-6-methyl-2-oxo-2H-chromene-3-yl]-N-[4-chloro-2-(trifluoromethyl)phenyl]acetamide (500 mg) in DMF (5 ml) was combined with methyl acrylate (0.14 ml), triethylamine (0.21 ml), pd(OAc)2 (5 ml) and triphenylphosphine (10 mg) under argon atmosphere, and heated at 120° C. for 3 hours. After the reaction was completed, the mixture was combined with water, and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and then concentrated. The resultant residue was purified by a silica gel chromatography (eluent: hexane-ethyl acetate=2:1), and then recrystallized from THF-ethyl acetate to obtain the title compound as a colorless crystal (333 mg, yield: 67%). Melting point: 202-204° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resultant residue was purified by a silica gel chromatography (eluent: hexane-ethyl acetate=2:1)
  6. customrecrystallized from THF-ethyl acetate

Sources & evidence

ORD record
ord-a5b46a8ff36a49a4a23ed08eeea91850
Source dataset
uspto-grants-2005_12
Patent number
US06974806B2

Reaction notes

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