Diisopropylamine → HCID 22506549, compound

HRID 985367Notes

Reaction equation

HRID 985367 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]#[CH:9])[N:5]=[C:4]([O:10][C:11]2[N:15]([CH3:16])[N:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[CH:3]=1.[F:21][C:22](F)(F)[C:23]1C=CC(I)=C[CH:24]=1.C(N[CH:36]([CH3:38])[CH3:37])(C)C>CCCCC.C(OCC)(=O)C.[Cu](I)I>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:37]2[CH:36]=[CH:38][C:22]([F:21])=[CH:23][CH:24]=2)[N:5]=[C:4]([O:10][C:11]2[N:15]([CH3:16])[N:14]=[C:13]([C:17]([F:19])([F:20])[F:18])[CH:12]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 7912DiisopropylamineHCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 12137492HCID 12137492, compound

Product 1

HCID 22506549HCID 22506549, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 22335286Ethyl acetate pentaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-methyl-6-ethynyl-2-(1-methyl-3-trifluorome-thylpyrazol-5-yloxy)pyridine (1 g, 3.55 mmol) in diisopropylamine (20 ml) under a nitrogen atmosphere are added 4-trifluoromethyl-iodobenzene (1.11 g, 5 mmol), bistriphenylphosphine palladium dichloride (0.12 g, 0.177 mmol) and copper iodide (0.02, 0.1 mmol) and the mixture is heated at 70 ° C. for 30 min. After cooling, the reaction mixture is diluted with pentane : ethyl acetate 1:1 and the organic phase is washed with water, diluted hydrochloric acid and a saturated aqueous solution of sodium bicarbonate and dried. 81% of the product (1.1 g, mp. 86-87° C.) is obtained by flash chromatography.

Workup

  1. temperatureAfter cooling
  2. washthe organic phase is washed with water, diluted hydrochloric acid
  3. dry with materiala saturated aqueous solution of sodium bicarbonate and dried

Sources & evidence

ORD record
ord-697d1b9ca0c24b5b9eed2330877758c3
Source dataset
uspto-grants-2005_03
Patent number
US06872690B2

Reaction notes

Loading…