Triethylamine → HCID 70925668, 화합물

HRID 1851655노트

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HRID 1851655 반응식
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]

참가 물질

8

반응물 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 70925591HCID 70925591, 화합물

생성물 1

HCID 70925668HCID 70925668, 화합물수율 80.6%

시약·촉매·용매 4

HCID 11776Triphenylphosphine촉매HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-885654e5808d47788bcdba3e64b4ade9
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957213B2

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