Diisopropylamine → HCID 90370191, compound

HRID 2176015Notes

Reaction equation

HRID 2176015 reaction equation
O1CCOCC1.Br[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=1.[C:17]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)#[CH:18].C(NC(C)C)(C)C>[Cu]I.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C(OCC)(=O)C>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]([C:18]#[C:17][C:19]2[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=2)=[N:9][CH:10]=1)([O-:16])=[O:15]

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 312751,4-DioxaneHCID 782402-Bromo-5-nitropyridineHCID 640163Methyl 4-ethynylbenzoate

Product 1

HCID 90370191HCID 90370191, compoundYield 88.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418851HCID 178418851, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 20 mL of a dioxane solution including 2.0 g of 2-bromo-5-nitropyridine were added 1.58 g of methyl 4-ethynylbenzoate, 4.1 mL of N-isopropylpropan-2-amine and 281 mg of copper (I) iodide, and 504 mg of bis(tri-tert-butylphosphine)palladium(0) was further added thereto in an argon atmosphere, followed by stirring for 1 hour at room temperature. 50 ml of ethyl acetate was added to the reaction mixture, the precipitated insoluble material was collected by filtration, thereby obtaining 2.45 g of methyl 4-[(5-nitropyridin-2-yl)ethynyl]benzoate.

Workup

  1. additionwas further added
  2. filtrationthe precipitated insoluble material was collected by filtration

Sources & evidence

ORD record
ord-2d89b4ed9b9d466c8677efd5a4ecbbe0
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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