Potassium Carbonate → HCID 66778484, compound

HRID 2091387Notes

Reaction equation

HRID 2091387 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([N:23]([CH3:31])[CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:22])=[CH:17][CH:16]=3)[CH:11]([CH3:13])[CH3:12])=[C:7]([CH3:32])[C:6]=2[CH:33]=1.[CH3:34][O:35][C:36]1[N:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[CH3:34][O:35][C:36]1[N:41]=[CH:40][C:39]([C:2]2[CH:3]=[CH:4][C:5]3[O:9][C:8]([CH:10]([NH:14][C:15]4[CH:16]=[CH:17][C:18]([C:21]([N:23]([CH3:31])[CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:22])=[CH:19][CH:20]=4)[CH:11]([CH3:13])[CH3:12])=[C:7]([CH3:32])[C:6]=3[CH:33]=2)=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 66777468HCID 66777468, compound2×

Product 1

HCID 66778484HCID 66778484, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution (10 mL) of ethyl 3-{[(4-{[1-(5-bromo-3-methyl-1-benzofuran-2-yl)-2-methylpropyl]amino}phenyl)carbonyl](methyl)amino}propanoate (0.55 g) synthesized in the above-mentioned (2) in N,N-dimethylacetamide were added (6-methoxypyridin-3-yl)boronic acid (0.33 g), potassium carbonate (0.29 g) and tetrakistriphenylphosphine palladium (0.12 g), and the mixture was stirred at 70° C. for 24 hr under argon atmosphere. The reaction mixture was cooled to room temperature, and filtered through celite, and the residue was washed with diethyl ether. Water was added to the filtrate, and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1, volume ratio) to give ethyl 3-[{[4-({1-[5-(6-methoxypyridin-3-yl)-3-methyl-1-benzofuran-2-yl]-2-methylpropyl}amino)phenyl]carbonyl}(methyl)amino]propanoate (0.10 g) as a pale-yellow oil. The obtained oil was dissolved in ethanol (1 mL), 1N aqueous sodium hydroxide solution (1.0 mL) was added to the solution at room temperature, and the mixture was stirred at room temperature for 0.5 hr. Ethanol was evaporated under reduced pressure, and 1N hydrochloric acid (1.0 mL) was added to the residue. The precipitate was washed with water to give the title object compound (0.06 g, 10%) as a colorless solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through celite
  3. washthe residue was washed with diethyl ether
  4. additionWater was added to the filtrate
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1, volume ratio)

Sources & evidence

ORD record
ord-ee8cd39f6ad94ea6ac50434e51183163
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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