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

HRID 606928

反応式

HRID 606928 の反応式
[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]

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178419050HCID 178419050、化合物触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-1237bf71b2dd440cace619e612230c93
出典データセット
uspto-grants-2011_03
特許番号
US07915424B2

関連ノート

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