Potassium Carbonate → HCID 24785929, compound

HRID 625995Notes

Reaction equation

HRID 625995 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][C:10]=2[O:18][CH3:19])=[N:6][CH:7]=1.[CH2:20]([OH:24])[CH2:21][C:22]#[CH:23].C([O-])([O-])=O.[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.[Pd].[Cu]I>[CH3:19][O:18][C:10]1[CH:11]=[C:12]([CH2:15][CH2:16][CH3:17])[CH:13]=[CH:14][C:9]=1[O:8][C:5]1[N:6]=[CH:7][C:2]([C:23]#[C:22][CH2:21][CH2:20][OH:24])=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 135663-Butyn-1-OLHCID 59191405HCID 59191405, compound

Product 1

HCID 24785929HCID 24785929, compoundYield 42.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-2-(2-methoxy-4-propylphenoxy)pyridine (0.19 mmol; 60 mg) under argon, in degased DME (1 mL) were added 3-butyn-1-ol (0.47 mmol; 33 mg), Pd/C (0.02 mmol; 42 mg), CuI (0.04 mmol; 7.6 mg), K2CO3 (0.47 mmol; 64 mg), and triphenylphosphine (0.08 mmol; 21 mg). The reaction mixture was stirred at 80° C. overnight, then filtered on celite, washed with ether (3 mL) then ethyl acetate (3 mL). Combined organic phases were washed with saturated NH4Cl (3 mL), dried over MgSO4, concentrated. The residue was purified by preparative TLC (dichloromethane/ethyl acetate) to yield the desired compound as a clear oil (25 mg; 0.08 mmol; 42%).

Workup

  1. filtrationfiltered on celite
  2. washwashed with ether (3 mL)
  3. washCombined organic phases were washed with saturated NH4Cl (3 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC (dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-bacd3ff65a5c47be8845f4ed3a5f0795
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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