Water → HCID 12433288, compound

HRID 1620029Notes

Reaction equation

Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].[C:10]([O:14][CH3:15])(=[O:13])[CH:11]=[CH2:12].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.O>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[NH2:6][C:5]1[CH:7]=[CH:8][C:2](/[CH:12]=[CH:11]/[C:10]([O:14][CH3:15])=[O:13])=[C:3]([CH3:9])[CH:4]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 4-bromo-3-methylaniline (5 g, TCI) in triethylamine (50 ml) was added with methyl acrylate (3.6 ml, TCI), tris(2-methylphenyl)phosphine (2.5 g, TCI), and palladium acetate (606 mg, WAKO), and stirred at 90° C. for 18 hours. The reaction mixture was added with water (30 ml) and ethyl acetate (30 ml×2) for extraction, and then successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine, the organic layer was dried, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Yamazen, n-hexane:ethyl acetate=3:1), and the solvent was evaporated under reduced pressure by using a rotary evaporator to obtain the title compound (yield: 4.0 g).

Workup

washsuccessively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine
customthe organic layer was dried
customthe solvent was evaporated under reduced pressure
customThe residue was purified by column chromatography (Yamazen, n-hexane:ethyl acetate=3:1)
customthe solvent was evaporated under reduced pressure
customa rotary evaporator

Sources & evidence

ORD record: ord-8ccae22e970b4b4dbb1dcbe22651cbaf
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772327B2

Reaction notes

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