Sodium Carbonate → 4-(5-Trifluoromethyl-benzoxazole-2-yl)-[3,3']bipyridinyl

HRID 884913Notes

Reaction equation

HRID 884913 reaction equation
I[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[N:12]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23](B(O)O)[CH:22]=1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[F:18][C:17]([F:20])([F:19])[C:14]1[CH:15]=[CH:16][C:10]2[O:9][C:8]([C:7]3[CH:6]=[CH:5][N:4]=[CH:3][C:2]=3[C:23]3[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=3)=[N:12][C:11]=2[CH:13]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27343783-Pyridinylboronic acidHCID 668805972-(3-Iodopyridin-4-yl)-5-(trifluoromethyl)benzoxazole

Product 1

HCID 668805224-(5-Trifluoromethyl-benzoxazole-2-yl)-[3,3']bipyridinylYield 102.9%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×

Procedure

To a mixture of 0.40 g of 2-(3-iodopyridin-4-yl)-5-(trifluoromethyl)benzoxazole, 0.21 g of 3-pyridine boronic acid, 8 ml of 1,4-dioxane and 0.07 g of dichlorobis(triphenylphosphine)palladium (II), a mixture of 0.40 g of sodium carbonate and 3 ml of water was added and heated to reflux for two hours. The reaction mixture was cooled to room temperature, and then water was added to the reaction mixture, followed by extraction with ethyl acetate. The combined organic layers were washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.36 g of 4-(5-trifluoromethyl-benzoxazole-2-yl)-[3,3′]bipyridinyl (hereinafter, referred to as “active compound 128”).

Workup

  1. additionwas added
  2. temperatureheated
  3. temperatureto reflux for two hours
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe combined organic layers were washed with water
  6. dry with materiala saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c823d252b894618af5363f0612370b0
Source dataset
uspto-grants-2012_08
Patent number
US08242133B2

Reaction notes

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