Diethylamine → 5-bromo-2-(6-chloropyridin-3-yloxy)-N,N-diethylbenzamide

HRID 529390노트

반응식

HRID 529390 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH2:19]([NH:21][CH2:22][CH3:23])[CH3:20].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[C:6]([CH:10]=1)[C:7]([N:21]([CH2:22][CH3:23])[CH2:19][CH3:20])=[O:9]

참가 물질

7

반응물 5

HCID 8021DiethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 574756345-Bromo-2-(6-chloropyridin-3-yloxy)benzoic acid

생성물 1

HCID 574756355-bromo-2-(6-chloropyridin-3-yloxy)-N,N-diethylbenzamide수율 55.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

A mixture of 5-bromo-2-(6-chloropyridin-3-yloxy)benzoic acid (1.28 kg, 4.44 mol), diethylamine (461 mL, 4.44 mol), HOBT (600 g, 4.44 mol), DIPEA (1.547 L, 8.88 mol) in anhydrous DCM (8 L) was cooled to 0° C. EDCI (851.2 g, 4.44 mol) was added to the reaction mixture and it was stirred at 0° C. for 30 minutes and then at RT overnight. The reaction mixture was sequentially washed with aqueous NaHCO3, brine and water before being dried over MgSO4. Filtration and concentrated under reduced pressure provided a residue that was purified by silica gel chromatography (5-20% EtOAc in hexane) to provide 950 g of 5-bromo-2-(6-chloropyridin-3-yloxy)-N,N-diethylbenzamide.

후처리

  1. customat RT
  2. customovernight
  3. washThe reaction mixture was sequentially washed with aqueous NaHCO3, brine and water
  4. dry with materialbefore being dried over MgSO4
  5. filtrationFiltration
  6. concentrationconcentrated under reduced pressure
  7. customprovided a residue that
  8. customwas purified by silica gel chromatography (5-20% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-69a15350616049f7a29ee52c96070fc0
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346827B2

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