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

HRID 529390ノート

反応式

HRID 529390 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-69a15350616049f7a29ee52c96070fc0
出典データセット
uspto-grants-2016_05
特許番号
US09346827B2

反応ノート

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