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

HRID 890804

反応式

HRID 890804 の反応式
[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.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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8471Triethylamine触媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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), Cul (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).

後処理

  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)

出典と根拠

ORDレコード
ord-b56a5b6057d54f95ba3d316ea5a51b4b
出典データセット
uspto-grants-2006_02
特許番号
US06998423B2

関連ノート

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