Triethylamine → 5-Ethoxycarbonyl-2-trimethylsilylethynylpyridine

HRID 1814086

反応式

HRID 1814086 の反応式
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8](Cl)=[N:7][CH:6]=1)[CH3:2].[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[CH:9][C:8]([C:18]#[C:17][Si:14]([CH3:16])([CH3:15])[CH3:13])=[N:7][CH:6]=1)=[O:12])[CH3:2]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 516892Sodium BicarbonateHCID 2799611Ethyl 6-chloronicotinate

生成物 1

HCID 225043975-Ethoxycarbonyl-2-trimethylsilylethynylpyridine収率 93%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 6-chloronicotinic acid ethyl ester (1.92 g) in N,N-dimethylformamide (1 ml), trimethylsilylacetylene (2.0 g), bistriphenylphosphine palladium dichloride (210 mg), cuprous iodide (60 mg) and triethylamine (1.2 g) were added successively and the mixture was stirred in a sealed tube at 100° C. for 2 hours. After cooling, the reaction solution was poured into a saturated aqueous sodium hydrogencabonate solution, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 2.38 g of the desired product as a brown oil.

後処理

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was separated

出典と根拠

ORDレコード
ord-23cb354fc7f34a738922fca5e6c3ffdd
出典データセット
uspto-grants-2005_04
特許番号
US06875770B2

関連ノート

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