1-Butanol → HCID 121409857, compound

HRID 64538Notes

Reaction equation

HRID 64538 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=2[F:15])=[N:6][CH:7]=1.[Cl:16][C:17]1[CH:22]=[C:21]([CH3:23])[C:20](B2OC(C)(C)C(C)(C)O2)=[C:19]([CH3:33])[CH:18]=1.C(O)CCC.[OH-].[Li+]>O.C(O[Pd]OC(=O)C)(=O)C.C1(P(C2CCCCC2)C2C=C(C3C(C(C)C)=CC(C(C)C)=CC=3C(C)C)C=CC=2)CCCCC1>[Cl:16][C:17]1[CH:22]=[C:21]([CH3:23])[C:20]([C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=3[F:15])=[N:6][CH:7]=2)=[C:19]([CH3:33])[CH:18]=1

Participants

8

Reactant 4

HCID 2631-ButanolHCID 3939Lithium HydroxideHCID 574612425-Bromo-2-(2,4-difluorophenyl)pyridineHCID 1300586982-(4-Chloro-2,6-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 121409857HCID 121409857, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 71309965Phosphine, dicyclohexyl(2',4',6'-tris(1-methylethyl)(1,1'-biphenyl)-3-yl)-CatalystHCID 962WaterSolvent

Procedure

One 100 mL round-bottomed flask was charged with 5-bromo-2-(2,4-difluorophenyl)pyridine (0.5 g, 1.851 mmol), 2-(4-chloro-2,6-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.730 g, 2.74 mmol), dicyclohexyl(2′,4′,6′-triisopropyl-[1,1′-biphenyl]-3-yl)phosphine (0.021 g, 0.044 mmol), diacetoxypalladium (8.31 mg, 0.037 mmol), and butanol (Volume: 6 ml) to give a yellow suspension. The reaction mixture was then stirred for 15 minutes at room temperature. Lithium hydroxide (0.075 g, 3.15 mmol) was added into reaction mixture and then heated to 80° C. for 1 hour. The reaction mixture was then diluted with deionized water and extracted by ethyl acetate. The organic portion was combined and subjected to column chromatography (SiO2 gel, 5% EtOAc in heptane) to yield the desired compound, 5-(4-chloro-2,6-dimethylphenyl)-2-(2,4-difluorophenyl)pyridine (0.525 g, 86%).

Workup

  1. customto give a yellow suspension
  2. temperatureheated to 80° C. for 1 hour
  3. extractionextracted by ethyl acetate

Sources & evidence

ORD record
ord-f9fa7ccdbcb04204baa3c01a9826cecd
Source dataset
uspto-grants-2016_09
Patent number
US09450195B2

Reaction notes

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