Triethylamine → Methyl 4-[2-(3,4,5-trimethoxy-phenylcarbamoyl)-vinyl]-benzoate

HRID 1180802Notes

Reaction equation

N1(O[C:11]([CH:13]=[CH:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)=[O:12])C2C=CC=CC=2N=N1.CCN(CC)CC.[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH:38]=[C:39]([O:43][CH3:44])[C:40]=1[O:41][CH3:42])[NH2:37]>C(Cl)Cl>[CH3:44][O:43][C:39]1[CH:38]=[C:36]([NH:37][C:11]([CH:13]=[CH:14][C:15]2[CH:16]=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:23][CH:24]=2)=[O:12])[CH:35]=[C:34]([O:33][CH3:32])[C:40]=1[O:41][CH3:42]

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred suspension at room temperature of VIII (150 mg, 0.46 mmol) in anhydrous CH2Cl2 (10 ml) under nitrogen were added Et3N (194 μl, 1.39 mmol) and 3,4,5-trimethoxyaniline (94 mg, 0.51 mmol) or ArNH2(1.1–1.2 equiv.), respectively. The reaction mixture was heated to 60° C. After 20 h, the reaction mixture was concentrated, diluted with AcOEt, and successively washed with a saturated aqueous solution of NH4Cl, H2O and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (AcOEt/CH2Cl2:15/85→20/80) to give the title product IXa (130 mg, 0.35 mmol, 75% yield) as a yellow solid. 1H NMR (300 MHz, acetone-d6) δ(ppm): 9.42 (bs, 1H), AB system (δA=8.09, δB=7.78, J=8.1 Hz, 4H), 7.75 (d, J=15.6 Hz, 1H), 7.21 (s, 2H), 7.00 (d, J=15.8 Hz, 1H), 3.94 (s, 3H), 3.85 (s, 6H), 3.73 (s, 3H).

Workup

concentrationthe reaction mixture was concentrated
additiondiluted with AcOEt
washsuccessively washed with a saturated aqueous solution of NH4Cl, H2O and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by flash chromatography on silica gel (AcOEt/CH2Cl2:15/85→20/80)

Sources & evidence

ORD record: ord-923b474ece4d4a9a8e4ab6c444ef5394
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07282608B2

Reaction notes

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