Triethylamine → 3-Chloro-5-(4-fluoro-3-methylphenylethynyl)-pyridine

HRID 606888

반응식

HRID 606888 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([F:9])=[C:5]([CH3:10])[CH:4]=1)#[CH:2].C(N(CC)CC)C.[Cl:18][C:19]1[CH:20]=[C:21](OS(C(F)(F)F)(=O)=O)[CH:22]=[N:23][CH:24]=1>C(OCC)(=O)C.[Cu]I.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>[Cl:18][C:19]1[CH:24]=[N:23][CH:22]=[C:21]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][C:6]([F:9])=[C:5]([CH3:10])[CH:4]=2)[CH:20]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 151858705-Chloropyridin-3-yl trifluoromethanesulfonateHCID 162137974-Ethynyl-1-fluoro-2-methylbenzene

생성물 1

HCID 670478013-Chloro-5-(4-fluoro-3-methylphenylethynyl)-pyridine수율 44%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178419050HCID 178419050, 화합물촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

Add 4-ethynyl-1-fluoro-2-methylbenzene (0.56 g, 4.21 mmol), triethylamine (2.2 mL, 15 mmol), copper (I) iodide (36 mg, 0.19 mmol), and bis(triphenylphosphine)palladium (II) dichloride (110 mg, 0.15 mmol) to a solution of trifluoromethanesulfonic acid 5-chloropyridin-3-yl ester, (prepared as described in PREPARATION 25), (1.0 g, 3.8 mmol) in ethyl acetate (5 mL) under nitrogen. Heat the at 70° C. for 16 h and concentrate. Purify by silica gel chromatography, eluting with 100% dichloromethane, followed by a second silica gel chromatography eluting with 50:50 to 60:40 dichloromethane:hexanes, to give the title compound as a light yellow solid (410 mg, 44%).

후처리

  1. concentrationconcentrate
  2. customPurify by silica gel chromatography
  3. washeluting with 100% dichloromethane
  4. washeluting with 50:50 to 60:40 dichloromethane

출처 및 근거

ORD 기록
ord-111deb5bc23f43d6822ed2d4aef65921
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915424B2

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