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

HRID 1891343노트

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HRID 1891343 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매2회

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온도
-78 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-32b1e8e1e1d94adeb5290241575ad872
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507536B2

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