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

HRID 76177

反応式

HRID 76177 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-80a171854e3a4cd182eb4751a6186526
出典データセット
uspto-grants-2014_09
特許番号
US08835472B2

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