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

HRID 1403670ノート

反応式

HRID 1403670 の反応式
[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]

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 311Citric Acid溶媒HCID 962Water溶媒HCID 86587095Dimethoxyethane ethanol water溶媒

反応条件

温度
130 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-fda90fd4ed6545158ee75d226cf37f77
出典データセット
uspto-grants-2014_12
特許番号
US08912209B2

反応ノート

読み込み中…