Tetrahydrofuran → 5-(3-Fluorophenylethynyl)-nicotinic acid ethyl ester

HRID 606799

반응식

HRID 606799 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.I[C:25]1[CH:26]=[C:27]([F:31])[CH:28]=[CH:29][CH:30]=1.[CH2:32]([O:34][C:35](=[O:48])[C:36]1[CH:41]=[C:40]([C:42]#[C:43][Si](C)(C)C)[CH:39]=[N:38][CH:37]=1)[CH3:33].[Cl-].[NH4+]>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>[CH2:32]([O:34][C:35](=[O:48])[C:36]1[CH:41]=[C:40]([C:42]#[C:43][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)[CH:39]=[N:38][CH:37]=1)[CH3:33]

참가 물질

9

반응물 5

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 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 3

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

실험 절차

Add a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.88 g, 3.38 mmol) to a mixture of 3-iodofluorobenzene (0.50 g, 2.25 mmol), 5-trimethylsilanylethynyl-nicotinic acid ethyl ester (0.84 g, 3.38 mmol), (prepared essentially as described in PREPARATION 16), bis(triphenylphosphine)palladium (II) dichloride (0.03 g, 0.05 mmol) and copper (I) iodide (0.02 g, 0.09 mmol) at −780C. Warm to room temperature, stir overnight and dilute the mixture with ethyl acetate and an aqueous saturated solution of ammonium chloride. Separate the organic layer; dry (magnesium sulfate), filter and concentrate. Purify the resulting 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 g, 80%).

후처리

  1. custom(prepared essentially
  2. customSeparate the organic layer
  3. dry with materialdry (magnesium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the resulting residue by silica gel chromatography
  7. washeluting with 2.5:45:52.5 ethyl acetate

출처 및 근거

ORD 기록
ord-a0fe3f254a904a1c9d2c2616b051a16f
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915424B2

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