Sodium Carbonate → HCID 60198794, compound

HRID 76382

Reaction equation

HRID 76382 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

HCID 60198794HCID 60198794, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-c62d31b447de42588a5de4dbc9c4fcc4
Source dataset
uspto-grants-2014_09
Patent number
US08835637B2

Linked notes

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