Triethylamine → HCID 70925668、化合物

HRID 1503272ノート

反応式

HRID 1503272 の反応式
I[C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:12][C:11]([CH3:14])([CH3:13])[N:10]([CH3:15])[C:9]2=[O:16])=[N:6][CH:7]=1.[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)#[CH:18].C(N(CC)CC)C>C1COCC1.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.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:15][N:10]1[C:11]([CH3:14])([CH3:13])[CH2:12][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([C:18]#[C:17][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:7][N:6]=2)[C:9]1=[O:16]

参加物

8

反応物 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 70925591HCID 70925591、化合物

生成物 1

HCID 70925668HCID 70925668、化合物収率 80.6%

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

A solution of (RS)-3-(5-iodopyridin-2-yl)-1,5,5-trimethylpyrrolidin-2-one (140 mg, 0.42 mmol), ethynylbenzene (65.0 mg, 69.9 μl, 0.64 mmol), triethylamine (129 mg, 177 μl, 1.27 mmol), bis(triphenylphosphine)palladium (II) chloride (17.9 mg, 25.4 μmol) and triphenylphosphine (3.34 mg, 12.7 μmol) in 4 ml of THF was purged with argon. Then copper (I) iodide (2.42 mg, 12.7 μmol) was added and the reaction was heated for 3 h at 60° C. After extraction with ethyl acetate/water, drying over sodium sulfate and concentration; the residue was taken up in ethyl acetate, adsorbed onto 3 g of silicagel which was loaded onto a 20 g prepacked flash chromato-graphy column. After elution with a 0% to 65% ethyl acetate in heptane gradient, the fractions containing the desired product were collected to yield 103 mg (72%) of the title compound as an amorphous yellow solid, MS: m/e=305.2 (M+H+).

後処理

  1. extractionAfter extraction with ethyl acetate/water
  2. dry with materialdrying over sodium sulfate and concentration
  3. washAfter elution with a 0% to 65% ethyl acetate in heptane gradient
  4. additionthe fractions containing the desired product
  5. customwere collected

出典と根拠

ORDレコード
ord-1a74b924ed5142618c20a103de709862
出典データセット
uspto-grants-2015_12
特許番号
US09212171B2

反応ノート

読み込み中…