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Sodium Carbonate → [2-((E)-3-{1-[4-(1-Methyl-1H-pyrazol-4-yl)-benzenesulfonyl]-1H-pyrrol-3-yl}-allanoylamino)-phenyl]-carbamic acid tert-butyl ester

HRID 2408445
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HRID 2408445 반응식
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:33])/[CH:16]=[CH:17]/[C:18]1[CH:22]=[CH:21][N:20]([S:23]([C:26]2[CH:31]=[CH:30][C:29](Br)=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:19]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:35][N:36]1[CH:40]=[C:39](B2OC(C)(C)C(C)(C)O2)[CH:38]=[N:37]1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:33])/[CH:16]=[CH:17]/[C:18]1[CH:22]=[CH:21][N:20]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([C:39]3[CH:38]=[N:37][N:36]([CH3:35])[CH:40]=3)=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:19]=1)([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 86621696(2-{(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-allanoylamino}-phenyl)-carbamic acid tert-butyl ester

생성물 1

HCID 67095603[2-((E)-3-{1-[4-(1-Methyl-1H-pyrazol-4-yl)-benzenesulfonyl]-1H-pyrrol-3-yl}-allanoylamino)-phenyl]-carbamic acid tert-butyl ester

시약·촉매·용매 1

HCID 8071
1,2-Dimethoxyethane
용매

실험 절차

(2-{(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-allanoylamino}-phenyl)-carbamic acid tert-butyl ester (3.0 g) and 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (1.71 g) are dissolved in DME (93 mL), (Ph3P)3PdCl2 (580 mg) and 2M Na2CO3-solution (55 mL) are added and the resulting mixture is heated under reflux temperature under an inert gas atmosphere. The solution is filtered and evaporated. The residue is treated with water and dichloromethane. The organic phase is separated, dried and evaporated. The crude product is purified by silica gel flash chromatography. The title compound is obtained in 902 mg yield.

후처리

  1. temperaturethe resulting mixture is heated
  2. temperatureunder reflux temperature under an inert gas atmosphere
  3. filtrationThe solution is filtered
  4. customevaporated
  5. additionThe residue is treated with water and dichloromethane
  6. customThe organic phase is separated
  7. customdried
  8. customevaporated
  9. customThe crude product is purified by silica gel flash chromatography

출처 및 근거

ORD 기록
ord-60994eb0a2754a41967c17dda192f15e
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08815855B2

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