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

HRID 2211664노트

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HRID 2211664 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매

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온도
100 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-467be4e71881463fa5aad2e5640c0d28
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101868B2

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