3-Ethynylbenzoic acid methyl ester → Methyl 3-((4-(2-acetamidopropyl)phenyl)ethynyl)benzoate

HRID 76177

반응식

HRID 76177 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])#[CH:2].I[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([NH:23][C:24](=[O:26])[CH3:25])[CH3:22])=[CH:16][CH:15]=1>CN(C=O)C.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:24]([NH:23][CH:21]([CH3:22])[CH2:20][C:17]1[CH:18]=[CH:19][C:14]([C:2]#[C:1][C:3]2[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=2)[C:6]([O:8][CH3:9])=[O:7])=[CH:15][CH:16]=1)(=[O:26])[CH3:25]

참가 물질

6

반응물 2

HCID 112751593-Ethynylbenzoic acid methyl esterHCID 66611344N-(1-(4-Iodophenyl)propan-2-YL)acetamide

생성물 1

HCID 66611163Methyl 3-((4-(2-acetamidopropyl)phenyl)ethynyl)benzoate

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 6228Dimethylformamide용매

실험 절차

To 10.0 g (63.4 mmol) methyl 3-ethynylbenzoate (J. Org. Chem. 1981, 46, 2280-6) and 7.00 g (23.1 mmol) N-(1-(4-iodo-phenyl)propan-2-yl)acetamide (I52.1) in 80 mL DMF are added 100 mL TEA, 250 mg (1.31 mmol) CuI and 1.20 g (1.71 mmol) bis(triphenylphosphine)-palladium (II) chloride. After stirring over night r.t. the solvents are removed under reduced pressure. The residue is partitioned between EtOAc and diluted aq. NH4Cl solution. The organic layer is separated and the aq. layer is extracted with EtOAc (2×). The org. layers are combined, washed with brine, dried with Na2SO4 and the solvent is removed in vacuo. The residue is purified by column chromatography (silica gel, EtOAc 100%).

후처리

  1. customare removed under reduced pressure
  2. customThe residue is partitioned between EtOAc and diluted aq. NH4Cl solution
  3. customThe organic layer is separated
  4. extractionthe aq. layer is extracted with EtOAc (2×)
  5. washwashed with brine
  6. dry with materialdried with Na2SO4
  7. customthe solvent is removed in vacuo
  8. customThe residue is purified by column chromatography (silica gel, EtOAc 100%)

출처 및 근거

ORD 기록
ord-80a171854e3a4cd182eb4751a6186526
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835472B2

연결된 노트

불러오는 중…