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

HRID 606799

反応式

HRID 606799 の反応式
[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]

参加物

9

反応物 5

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 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 3

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

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-a0fe3f254a904a1c9d2c2616b051a16f
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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