3-(Methoxycarbonyl)benzeneboronic acid → Methyl 2-amino-5-({1-[3-(methoxycarbonyl)phenyl]-2-methylindolizin-3-yl}carbonyl)benzoate

HRID 535446노트

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HRID 535446 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1)=[O:4].O.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[NH2:24][C:25]1[CH:34]=[CH:33][C:32]([C:35]([C:37]2[N:45]3[C:40]([CH:41]=[CH:42][CH:43]=[CH:44]3)=[C:39](Br)[C:38]=2[CH3:47])=[O:36])=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:24][C:25]1[CH:34]=[CH:33][C:32]([C:35]([C:37]2[N:45]3[C:40]([CH:41]=[CH:42][CH:43]=[CH:44]3)=[C:39]([C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:10]=3)[C:38]=2[CH3:47])=[O:36])=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28]

참가 물질

6

반응물 3

HCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 23436936Potassium phosphate dihydrateHCID 57500395Methyl 2-amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]benzoate

생성물 1

HCID 66653153Methyl 2-amino-5-({1-[3-(methoxycarbonyl)phenyl]-2-methylindolizin-3-yl}carbonyl)benzoate수율 65.9%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 18180031Water 1,2-dimethoxyethane용매

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온도
90 °C

실험 절차

0.229 g (1.27 mmol) of [3-(methoxycarbonyl)phenyl]boronic acid, 0.492 g (2.12 mmol) of potassium phosphate dihydrate and 0.024 g (0.02 mmol) of tetrakis(triphenylphosphine)palladium are added, under an argon atmosphere at ambient temperature, to 0.410 g (1.06 mmol) of methyl 2-amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]benzoate in 8 ml of a DME/H2O (5/1) mixture. The reaction medium is heated at 90° C. for 18 hours. The reaction medium is extracted with dichloromethane, washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate, filtered, and then concentrated under reduced pressure. The solid obtained is purified by silica gel column chromatography, elution being carried out with dichloromethane. 309 mg of a yellow solid are obtained.

후처리

  1. extractionThe reaction medium is extracted with dichloromethane
  2. washwashed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe solid obtained
  7. customis purified by silica gel column chromatography, elution

출처 및 근거

ORD 기록
ord-ca3aab6099ff4c8bba625c3ea634d623
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859544B2

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