Triethylamine → 3-(4-(4-Phenylthiazol-2-yl)but-3-yn-1-yl)benzonitrile

HRID 1397367노트

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HRID 1397367 반응식
[CH2:1]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[C:8]#[N:9])[CH2:2][C:3]#[CH:4].Br[C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:18]=1.CCN(CC)CC>CN(C=O)C.[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:19]1([C:17]2[N:18]=[C:14]([C:4]#[C:3][CH2:2][CH2:1][C:5]3[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=3)[C:8]#[N:9])[S:15][CH:16]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 99211062-Bromo-4-phenyl-1,3-thiazoleHCID 541923053-(But-3-yn-1-yl)benzonitrile

생성물 1

HCID 673238153-(4-(4-Phenylthiazol-2-yl)but-3-yn-1-yl)benzonitrile수율 50.5%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

3-(But-3-yn-1-yl)benzonitrile (462 mg, 2.98 mmol) and 2-bromo-4-phenylthiazole (650 mg, 2.71 mmol) were taken in dry DMF (20 mL) and purged with nitrogen gas for 15 min. Et3N (1.9 mL, 13.5 mmol) was added to the reaction mixture, followed by a catalytic amount of copper iodide (51 mg, 0.27 mmol) and Pd(PPh3)4 (115 mg, 0.1 mmol). The reaction mixture was stirred at room temperature for 12 h and then quenched with water. The organic product was extracted with EtOAc, and the combined extracts were concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluant 15-20% EtOAc in petroleum ether) to get 3-(4-(4-phenylthiazol-2-yl)but-3-yn-1-yl)benzonitrile (430 mg, yield 50%) as a pale yellow solid. 1H NMR (300 MHz, CDCl3) δ 7.92-7.90 (m, 2H), 7.59-7.52 (m, 3H), 7.47-7.33 (m, 5H), 3.04-2.99 (m, 2H), 2.83-2.78 (m, 2H). MS (ESI) m/z: Calculated for C20H14N2S: 314.09. found: 315.2 (M+H)+.

후처리

  1. custompurged with nitrogen gas for 15 min
  2. customquenched with water
  3. extractionThe organic product was extracted with EtOAc
  4. concentrationthe combined extracts were concentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (silica 60-120 mesh, eluant 15-20% EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-3efd9e325fdd4bf0872fe6eaa4889af6
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901156B2

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