tert-Butyl isocyanate → (5-Bromo-4-methylpyridin-2-yl)-n-t-butyl carboxylic amide

HRID 661606

反応式

HRID 661606 の反応式
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:9])=[CH:4][N:3]=1.[Li]CCCC.[C:15]([N:19]=[C:20]=[O:21])([CH3:18])([CH3:17])[CH3:16]>C1(C)C=CC=CC=1>[Br:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([C:20]([NH:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])=[N:3][CH:4]=1

参加物

5

反応物 3

HCID 62412tert-Butyl isocyanateHCID 27344292,5-Dibromo-4-methylpyridineHCID 178418339Butyllithium

生成物 1

HCID 68468634(5-Bromo-4-methylpyridin-2-yl)-n-t-butyl carboxylic amide

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
-78 °C

実験手順

2,5-Dibromo-4-methylpyridine (1.83 g, 7.29 mmol) was dissolved in toluene (100 mL), cooled to −78° C. and a solution of nBuLi (4.4 mL, 8.8 mmol, 2.0 M in pentane) was added dropwise and stirred at −78° C. for 2 h. A solution of tBuNCO (1.1 mL, 9.5 mmol) in toluene (3 mL) was added dropwise and stirred for 1 h at −78° C. then warmed to −10° C. and quenched by addition of NH4Cl (aq). After warming to r.t. the reaction was extracted with ether and the organics dried over Na2SO4 and concentrated. The product was used without further purification. MS [M+H]+: 271.0; tR=2.44 min. (method 1)

後処理

  1. stirringstirred for 1 h at −78° C.
  2. temperaturethen warmed to −10° C.
  3. customquenched by addition of NH4Cl (aq)
  4. temperatureAfter warming to r.t. the reaction
  5. extractionwas extracted with ether
  6. dry with materialthe organics dried over Na2SO4
  7. concentrationconcentrated
  8. customThe product was used without further purification

出典と根拠

ORDレコード
ord-fceb5ed9f77045c3b6fb0ee255652505
出典データセット
uspto-grants-2011_12
特許番号
US08084614B2

関連ノート

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