Sodium Carbonate → 2'-(1-tert-Butoxycarbonylamino-ethyl)-5'-(3-fluoro-pyridin-4-ylcarbamoyl)-biphenyl-3-carboxylic acid

HRID 2409369노트

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HRID 2409369 반응식
[C:1]([O:5][C:6](=[O:27])[NH:7][CH:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:25])[NH:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][C:19]=2[F:24])=[CH:12][C:11]=1Br)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[C:28]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)([OH:30])=[O:29].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.O.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)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>[C:1]([O:5][C:6]([NH:7][CH:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:25])[NH:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][C:19]=2[F:24])=[CH:12][C:11]=1[C:35]1[CH:34]=[CH:33][CH:32]=[C:31]([C:28]([OH:30])=[O:29])[CH:36]=1)[CH3:9])=[O:27])([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 27339573-Carboxyphenylboronic acidHCID 67407943{1-[2-Bromo-4-(3-fluoro-pyridin-4-ylcarbamoyl)-phenyl]-ethyl}-carbamic acid tert-butyl ester

생성물 1

HCID 674097672'-(1-tert-Butoxycarbonylamino-ethyl)-5'-(3-fluoro-pyridin-4-ylcarbamoyl)-biphenyl-3-carboxylic acid

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 311Citric Acid용매HCID 962Water용매HCID 86587095Dimethoxyethane ethanol water용매

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온도
130 °C

실험 절차

To a solution of {1-[2-bromo-4-(3-fluoro-pyridin-4-ylcarbamoyl)-phenyl]-ethyl}-carbamicacid tert-butyl ester (2841 μmol) and 3-carboxyphenylboronic acid (1.5 eq.) in a mixture of DME/EtOH/water:1/1/1 (10 ml) was added Na2CO3 (4 eq) and Pd tetrakis (0.05 eq). The reaction mixture was heated in the microwave at 130° C. for 1.5 hours. The reaction mixture was diluted with water and citric acid (to acidic pH) and extracted with EtOAc. The combined organic layers were dried over MgSO4 and the solvent was removed under reduced pressure. The compound was purified by column chromatography (silicagel, DCM/MeOH gradient).

후처리

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. customthe solvent was removed under reduced pressure
  4. customThe compound was purified by column chromatography (silicagel, DCM/MeOH gradient)

출처 및 근거

ORD 기록
ord-747c98d1b29c4dc285830831230468e8
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815873B2

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