Sodium Carbonate → HCID 60198794、化合物

HRID 76382

反応式

HRID 76382 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[C:11]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)([OH:13])=[O:12].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[C:11]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=2)=[CH:18][CH:17]=1)([OH:13])=[O:12]

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 6085445-Bromopyridine-2-carboxylic acidHCID 38634844-(2-Carboxyethyl)benzeneboronic acid

生成物 1

HCID 60198794HCID 60198794、化合物

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

Under an argon atmosphere, to 4 ml 1,2-dimethoxyethane are added 5-bromo-pyridine-2-carboxylic acid (93 mg, 0.46 mmol), 4-(2-carboxyethyl)benzeneboronic acid (106 mg, 0.55 mmol), 0.51 ml of a 2M aqueous sodium carbonate solution and dichlorobis-(triphenylphosphin) palladium (II) (20 mg, 0.03 mmol). The mixture is stirred at 90° C. overnight, cooled and quenched with water. Ethyl acetate is added and the mixture adjusted to pH=2 with 1M hydrochloric acid. After threefold extraction with ethyl acetate, the combined organic layers are dried over magnesium sulfate, filtered, and evaporated in vacuo. The residue is purified by silica gel chromatography (eluent:dichloromethane/methanol 5:1).

後処理

  1. temperaturecooled
  2. customquenched with water
  3. additionEthyl acetate is added
  4. extractionAfter threefold extraction with ethyl acetate
  5. dry with materialthe combined organic layers are dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue is purified by silica gel chromatography (eluent:dichloromethane/methanol 5:1)

出典と根拠

ORDレコード
ord-c62d31b447de42588a5de4dbc9c4fcc4
出典データセット
uspto-grants-2014_09
特許番号
US08835637B2

関連ノート

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