Triethylamine → 3-Fluoro-5-phenylethynylpyridine

HRID 606844노트

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HRID 606844 반응식
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[F:16][C:17]1[CH:18]=[C:19](OS(C(F)(F)F)(=O)=O)[CH:20]=[N:21][CH:22]=1>C(OCC)(=O)C.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:16][C:17]1[CH:22]=[N:21][CH:20]=[C:19]([C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:18]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 11413882Methanesulfonic acid, trifluoro-, 5-fluoro-3-pyridinyl ester

생성물 1

HCID 670474963-Fluoro-5-phenylethynylpyridine수율 65%

시약·촉매·용매 2

HCID 178419050HCID 178419050, 화합물촉매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

Add phenylacetylene (0.180 mL, 1.6 mmol), copper (I) iodide (0.015 g, 0.08 mmol) bis(triphenylphosphine)palladium (II) dichloride (0.027 g. 0.04 mmol) and triethylamine (0.85 mL, 6 mmol) to a solution of trifluoromethanesulfonic acid 5-fluoro-pyridin-3-yl ester, (prepared essentially as described in PREPARATION 6), (0.367 g, 1.5 mmol) in degassed ethyl acetate (1.5 mL) and heat at 60° C. for 16 h. Cool the reaction mixture to room temperature, filter through diatomaceous earth, wash with ethyl acetate, and concentrate. Purify the residue by silica gel chromatography, eluting with dichloromethane, to give the title compound (0.192 g, 65%).

후처리

  1. custom(prepared essentially
  2. temperatureCool the reaction mixture to room temperature
  3. filtrationfilter through diatomaceous earth
  4. washwash with ethyl acetate
  5. concentrationconcentrate
  6. customPurify the residue by silica gel chromatography
  7. washeluting with dichloromethane

출처 및 근거

ORD 기록
ord-55c22a639733475fa7dc8b4eaaabb4ef
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915424B2

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