Propargyl alcohol → (Tert-butoxy)-n-{[4-fluoro-3-(3-hydroxyprop-1-ynyl)phenyl]methyl}carboxamide

HRID 2211664ノート

反応式

HRID 2211664 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12](Br)[CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([OH:21])[C:19]#[CH:20]>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([C:20]#[C:19][CH2:18][OH:21])[CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 7859Propargyl alcoholHCID 21961437[(3-Bromo-4-fluorophenyl)methyl]-carbamic acid tert-butyl ester

生成物 1

HCID 131725909(Tert-butoxy)-n-{[4-fluoro-3-(3-hydroxyprop-1-ynyl)phenyl]methyl}carboxamide

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒

反応条件

温度
100 °C

実験手順

A mixture of tert-butoxy-N-[(3-bromo-4-fluorophenyl)methyl]carboxamide (0.6 g, 2.0 mmol, Step A), CuI (38 mg, 0.2 mmol), PdCl2(PPh3)2 (72 mg, 0.1 mmol), propargyl alcohol (0.35 mL, 6.0 mmol) and TEA (12 mL) was heated at 100° C. for 5 h. The resulting mixture was filtered, and the filtrate was concentrated. The residue was purified by SiO2 chromatography to give the title compound. MS (ES+): 297 (M+NH4)+. Calc'd C15H22FN2O3-297.34.

後処理

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by SiO2 chromatography

出典と根拠

ORDレコード
ord-467be4e71881463fa5aad2e5640c0d28
出典データセット
uspto-grants-2006_09
特許番号
US07101868B2

反応ノート

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