1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-bromo-2-(6-chloropyridin-3-yloxy)-N,N-diethylbenzamide

HRID 455547노트

반응식

HRID 455547 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.C1C=CC2N(O)N=NC=2C=1.[CH3:29][CH2:30][N:31](C(C)C)[CH:32](C)[CH3:33].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:31]([CH2:32][CH3:33])[CH2:30][CH3:29])=[O:9]

참가 물질

6

반응물 4

HCID 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 compound 5-bromo-2-(6-chloropyridin-3-yloxy)benzoic acid (1.28 Kg, 4.44 mol), DEA (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. and EDCI (851.2 g, 4.44 mol, 1 eq) was added. The mixture was stirred at 0° C. for 30 minutes and then at RT overnight. The reaction mixture was washed with an aqueous, saturated solution of NaHCO3, brine and water. The organic phase was separated, dried over MgSO4 and concentrated under reduced pressure. The resulting crude mixture was purified by silica gel chromatography (5 to 20% ethyl acetate in hexane) to afford 950 g of 5-bromo-2-(6-chloropyridin-3-yloxy)-N,N-diethylbenzamide as a yellow oil.

후처리

  1. customat RT
  2. customovernight
  3. washThe reaction mixture was washed with an aqueous, saturated solution of NaHCO3, brine and water
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting crude mixture was purified by silica gel chromatography (5 to 20% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-d94c5fe2e48c4bf2a5c03568cb04fc3c
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497264B2

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