Methyl 5-bromothiophene-2-carboxylate → 5-(3-tert-Butoxycarbonylamino-prop-1-ynyl)-thiophene-2-carboxylic Acid Methyl Ester

HRID 480343

반응식

HRID 480343 반응식
[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][C:9]#[CH:10])([CH3:4])([CH3:3])[CH3:2].[CH3:12][O:13][C:14]([C:16]1[S:17][C:18](Br)=[CH:19][CH:20]=1)=[O:15]>C(#N)C.CCOC(C)=O.[Cu]I.C(N(CC)CC)C>[CH3:12][O:13][C:14]([C:16]1[S:17][C:18]([C:10]#[C:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:11])=[CH:19][CH:20]=1)=[O:15]

참가 물질

7

반응물 2

HCID 605713Methyl 5-bromothiophene-2-carboxylateHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamate

생성물 1

HCID 540753395-(3-tert-Butoxycarbonylamino-prop-1-ynyl)-thiophene-2-carboxylic Acid Methyl Ester수율 63,406.199%

시약·촉매·용매 4

HCID 8471Triethylamine촉매HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of prop-2-ynyl-carbamic acid tert-butyl ester (1.67 g, 0.011 mmol), 5-bromo-thiophene-2-carboxylic acid methyl ester (2.50 g, 0.011 mmol), tetrakistriphenylphosphine(0) palladium (0.622 g, 0.0538 mmol), CuI (0.102 g, 0.538 mmol) and triethylamine (1.57 mL, 0.011 mmol) in 50 mL acetonitrile under nitrogen was heated at reflux for 16 h. The reaction was cooled to room temperature, diluted with 75 mL EtOAc, washed with 5.5% HCl, water and brine, dried over MgSO4, filtered and concentrated in vacuo to an oil. The product was purified via flash chromatography (9:1 to 4:1 hexanes:EtOAc) to afford the title compound as an oil (2.06 g). MS 313 (M+18).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. washwashed with 5.5% HCl, water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to an oil
  7. customThe product was purified via flash chromatography (9:1 to 4:1 hexanes:EtOAc)

출처 및 근거

ORD 기록
ord-6f54f91d847e41e6b7ab1df117abed0c
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06649657B2

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