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Sodium Carbonate → Tert-butyl 4-(3-(diethylamino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate

HRID 454770
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인쇄 미리보기

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HRID 454770 반응식
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([NH:15][C:16]([C:18]2[CH:19]=[N:20][CH:21]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:23]=2)=[O:17])[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:36]([N:38]([CH2:54][CH3:55])[C:39]1[CH:44]=[CH:43][CH:42]=[C:41](B2OC(C)(C)C(C)(C)O2)[CH:40]=1)[CH3:37]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(Cl)(Cl)Cl.O.COCCOC>[CH2:54]([N:38]([CH2:36][CH3:37])[C:39]1[CH:40]=[C:41]([C:2]2[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:11])([CH3:10])[CH3:12])=[O:7])=[C:4]([NH:15][C:16]([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:23]=3)=[O:17])[CH:3]=2)[CH:42]=[CH:43][CH:44]=1)[CH3:55]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 58508430Tert-butyl 4-bromo-2-(5-phenylpyridine-3-carboxamido)benzoateHCID 66990273N,N-diethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

생성물 1

HCID 66990777Tert-butyl 4-(3-(diethylamino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate수율 94.8%

시약·촉매·용매 4

HCID 178418476
HCID 178418476, 화합물
촉매
HCID 962Water용매2회
HCID 6212Chloroform용매
HCID 80711,2-Dimethoxyethane용매

실험 절차

Tert-butyl 4-bromo-2-(5-phenylpyridine-3-carboxamido)benzoate (0.11 g), sodium carbonate (64 mg), water (0.30 mL), and bis(triphenylphosphine)palladium(II) dichloride (3.5 mg) were added to an ethylene glycol dimethyl ether (1.0 mL) solution of N,N-diethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (83 mg), followed by heating to reflux under a nitrogen atmosphere for 2 hours and 40 minutes. The reaction mixture was cooled to room temperature, and then water and chloroform were added thereto. The organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 90-70% hexane/ethyl acetate] to obtain 0.12 g of tert-butyl 4-(3-(diethylamino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate as a yellow solid.

후처리

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 2 hours and 40 minutes
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography [eluent: 90-70% hexane/ethyl acetate]

출처 및 근거

ORD 기록
ord-27ae272f2e64466a8460117e0ce86feb
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08492582B2

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