Sodium Sulfate → (E)-3-{1-[4-(1-methyl-1H-indol-5-yl)-benzenesulfonyl]-1H-pyrrol-3-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide

HRID 2408441노트

반응식

HRID 2408441 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([NH:20][O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)=[O:19])=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:28][N:29]1[C:37]2[C:32](=[CH:33][C:34](B(O)O)=[CH:35][CH:36]=2)[CH:31]=[CH:30]1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C(COC)OC>[CH3:28][N:29]1[C:37]2[C:32](=[CH:33][C:34]([C:2]3[CH:7]=[CH:6][C:5]([S:8]([N:11]4[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([NH:20][O:21][CH:22]5[CH2:27][CH2:26][CH2:25][CH2:24][O:23]5)=[O:19])=[CH:12]4)(=[O:10])=[O:9])=[CH:4][CH:3]=3)=[CH:35][CH:36]=2)[CH:31]=[CH:30]1

참가 물질

6

반응물 3

HCID 24436Sodium SulfateHCID 27598671-Methyl-1H-indole-5-boronic acidHCID 86621691(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide

생성물 1

HCID 86621684(E)-3-{1-[4-(1-methyl-1H-indol-5-yl)-benzenesulfonyl]-1H-pyrrol-3-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide

시약·촉매·용매 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture of 0.4 g (E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide, 0.231 g N-Methylindol-5-boronic acid and 14 ml dimethoxyethane is slightly heated and to this mixture are added bis(triphenylphosphine)palladium(II)chloride and 1.5 ml of a 2M aqueous sodium sulfate solution. This mixture is heated to reflux temperature under an inert gas atmosphere overnight. After cooling the mixture is filtered, evaporated and the residue is partitioned between ethyl acetate and a 5% aqueous solution of sodium bicarbonate. The organic phase is dried and evaporated and the residue is purified by silica gel flash chromatography.

후처리

  1. temperatureis slightly heated and to this mixture
  2. temperatureThis mixture is heated
  3. temperatureto reflux temperature under an inert gas atmosphere overnight
  4. temperatureAfter cooling the mixture
  5. filtrationis filtered
  6. customevaporated
  7. customthe residue is partitioned between ethyl acetate
  8. customThe organic phase is dried
  9. customevaporated
  10. customthe residue is purified by silica gel flash chromatography

출처 및 근거

ORD 기록
ord-376ee4baf3c74b70bfbc6d38e36617f4
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815855B2

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