Sodium Carbonate → 5-[4-(2-Carboxy-ethyl)-phenyl]-pyridine-2-carboxylic acid

HRID 1478791노트

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HRID 1478791 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 601987945-[4-(2-Carboxy-ethyl)-phenyl]-pyridine-2-carboxylic acid

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3942a45665ac4f3cb781f888f7f0784f
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403859B2

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