Sodium Carbonate → HCID 60198794, 화합물

HRID 76382

반응식

HRID 76382 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 60198794HCID 60198794, 화합물

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-c62d31b447de42588a5de4dbc9c4fcc4
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835637B2

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