Diisopropylamine → HCID 67364555, compound

HRID 1916518Notes

Reaction equation

HRID 1916518 reaction equation
[CH2:1]([N:3]([CH2:15][CH3:16])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[CH:14])=[CH:9][CH:8]=1)[CH3:2].Br[C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][N:19]=1.C(N(C(C)C)C(C)C)C.C(NC(C)C)(C)C>CN(C=O)C.[Cu]I>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([C:14]#[C:13][C:10]2[CH:9]=[CH:8][C:7]([O:6][CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:15][CH3:16])=[CH:12][CH:11]=2)=[N:19][CH:20]=1

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 693532,5-DibromopyridineHCID 81531DiisopropylethylamineHCID 85969792HCID 85969792, compound

Product 1

HCID 67364555HCID 67364555, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 500 mg (2.30 mmol) diethyl-[2-(4-ethynyl-phenoxy)-ethyl]-amine, 545 mg (2.30 mmol) 2,5-dibromopyridine, 161 mg (0.23 mmol) tetrakis-triphenylphosphane-palladium, 13 mg (0.07 mmol) CuI, 2 mL ethyldiisopropylamine and 2 mL diisopropylamine in 50 mL DMF is heated for 20 h at 100° C. under a nitrogen atmosphere. The solvent is distilled off i.vac., the residue is taken up in water, exhaustively extracted with EtOAc and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified on silica gel (EtOAc/MeOH/NH3 95:5:0.5).

Workup

  1. distillationThe solvent is distilled off i.vac
  2. extractionexhaustively extracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. customis purified on silica gel (EtOAc/MeOH/NH3 95:5:0.5)

Sources & evidence

ORD record
ord-9685b56a81e242d09a0278154741cefb
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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