1-Fluoro-3-iodobenzene → 5-(3-Fluorophenylethynyl)-nicotinic acid ethyl ester

HRID 606928

반응식

HRID 606928 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.I[C:20]1[CH:21]=[C:22]([F:26])[CH:23]=[CH:24][CH:25]=1.[CH2:27]([O:29][C:30](=[O:43])[C:31]1[CH:36]=[C:35]([C:37]#[C:38][Si](C)(C)C)[CH:34]=[N:33][CH:32]=1)[CH3:28]>O1CCCC1.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.[Cu]I>[CH2:27]([O:29][C:30](=[O:43])[C:31]1[CH:36]=[C:35]([C:37]#[C:38][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)[CH:34]=[N:33][CH:32]=1)[CH3:28]

참가 물질

8

반응물 3

HCID 707251-Fluoro-3-iodobenzeneHCID 2724141Tetrabutylammonium FluorideHCID 67047749Ethyl 5-((trimethylsilyl)ethynyl)nicotinate

생성물 1

HCID 670477625-(3-Fluorophenylethynyl)-nicotinic acid ethyl ester수율 80%

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178419050HCID 178419050, 화합물촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Add a 1 M solution of tetrabutylammonium fluoride (0.88 g, 3.38 mmol) in tetrahydrofuran to a mixture of 3-iodofluorobenzene (0.50 g, 2.25 mmol), 5-trimethylsilanylethynyl-nicotinic acid ethyl ester, (prepared as described in PREPARATION 16), (0.84 g, 3.38 mmol), bis(triphenylphosphine)palladium (II) dichloride (0.03 g, 0.05 mmol) and copper (I) iodide (0.02 g, 0.09 mmol) at −78° C. Warm to room temperature, stir overnight and then dilute with ethyl acetate. Wash with an aqueous saturated solution of ammonium chloride, dry (magnesium sulfate), filter and concentrate. Purify the residue by silica gel chromatography, eluting with 2.5:45:52.5 ethyl acetate:chloroform:hexanes, to give the title compound as a pale yellow solid (0.46 mg, 80%).

후처리

  1. washWash with an aqueous saturated solution of ammonium chloride
  2. dry with materialdry (magnesium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the residue by silica gel chromatography
  6. washeluting with 2.5:45:52.5 ethyl acetate

출처 및 근거

ORD 기록
ord-1237bf71b2dd440cace619e612230c93
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915424B2

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