Triethylamine → Ethyl 5-(2-phenyleth-1-ynyl)nicotinate

HRID 391508노트

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HRID 391508 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(N(CC)CC)C.[C:20]1([C:26]#[CH:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)(=O)C.[Cu](I)I>[CH2:10]([O:9][C:7](=[O:8])[C:6]1[CH:12]=[C:2]([C:27]#[C:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:3]=[N:4][CH:5]=1)[CH3:11]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 140785Ethyl 5-bromopyridine-3-carboxylate

생성물 1

HCID 2779231Ethyl 5-(2-phenyleth-1-ynyl)nicotinate수율 100.3%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

To a solution of ethyl 5-bromonicotinate (1.15 g, 5 mmol) in ethyl acetate (20 mL) under an N2 atmosphere, was added triethylamine (1.1 mL, 7.5 mmol, 1.5 eq.), phenyl acetylene (0.766 g, 7.5 mmol, 1.5 eq.), dichloro-bis(triphenylphosphine)-palladium(II) (176 mg, 0.25 mmol, 0.05 eq.), and copper iodide (10 mg, 0.05 mmol, 0.01 eq). The reaction mixture was heated at 50° C. for 20 h before being cooled to room temperature, filtered through a pad of celite, and solvent evaporated to provide a dark brown oil. Silica gel column chromatography (9/1-4/1 hexanes/EtOAc elution) provided the title compound as a pale yellow oil (1.26 g, yield 100%). 1H NMR (300 MHz, CDCl3) δ 9.11 (d, J=1.8 Hz, 1H), 8.87 (d, J=2.1 Hz, 1H), 8.39 (dd, J=1.8, 2.1 Hz, 1H), 7.56-7.53 (m, 2H), 7.40-7.30 (m, 3H), 4.42 (q, J=7.2 Hz, 2H), 1.43 (t, J=7.2 Hz, 3H); ESI-MS m/z 251.9 (M+H)+.

후처리

  1. temperaturebefore being cooled to room temperature
  2. filtrationfiltered through a pad of celite, and solvent
  3. customevaporated
  4. customto provide a dark brown oil
  5. washSilica gel column chromatography (9/1-4/1 hexanes/EtOAc elution)

출처 및 근거

ORD 기록
ord-e8f4bf834fc34fad8fe2108ded524231
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383825B2

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