Triethylamine → [4-(4-Cyanophenyl)but-3-ynyl]carbamic acid tert-butyl ester

HRID 217945

반응식

HRID 217945 반응식
[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][C:10]#[CH:11])([CH3:4])([CH3:3])[CH3:2].I[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1.C(N(CC)CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C1COCC1>[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][C:10]#[C:11][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 764674-IodobenzonitrileHCID 10725815tert-Butyl 3-butyn-1-ylcarbamate

생성물 1

HCID 67364707[4-(4-Cyanophenyl)but-3-ynyl]carbamic acid tert-butyl ester수율 99%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

But-3-ynylcarbamic acid tert-butyl ester (3.66 g, 22 mmol) was added dropwise to an ice cooled, stirring, argon purged mixture of 4-iodobenzonitrile (4.5 g, 19.6 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.69 g, 0.98 mmol), copper (I) iodide (0.19 g, 0.98 mmol), triethylamine (11 mL, 78.4 mmol), and THF (24 mL). After stirring for 10 min, the ice bath was removed, and the reaction was allowed to stir for an additional 2 h. The reaction mixture was passed through a pad of silica gel with methylene chloride/ethyl acetate (5:1) as eluant. After evaporating the solvent, the crude product was chromatographed with methylene chloride/ethyl acetate (20:1) as eluant. Evaporation of the solvent, followed by placement under vacuum for 1 h, afforded the pure product 56 (5.2 g, 99%) as an oil. 1H NMR (300 MHz, CDCl3) δ 1.46 (s, 9H), 2.64 (t, 2H), 3.37 (m, 2H), 4.85 (br s, 1H), 7.47 (d, 2H), 7.58 (d, 2H).

후처리

  1. temperaturecooled
  2. customargon purged
  3. stirringAfter stirring for 10 min
  4. customthe ice bath was removed
  5. stirringto stir for an additional 2 h
  6. customAfter evaporating the solvent
  7. customthe crude product was chromatographed with methylene chloride/ethyl acetate (20:1) as eluant
  8. customEvaporation of the solvent

출처 및 근거

ORD 기록
ord-35c8a3e01b1c4c9e88804df2bb4ed36e
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198286B2

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