Sodium Carbonate → 4-[5-(4-Chloro-phenyl)-pyridin-2-yl]-2-methyl-but-3-yn-2-ol

HRID 1916724Notes

Reaction equation

C([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]([CH3:19])([OH:18])[CH3:17])=[N:12][CH:13]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24](OB(O)O)=[CH:23][CH:22]=1>O1CCOCC1>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]([CH3:19])([OH:18])[CH3:17])=[N:12][CH:13]=2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 85 °C

Procedure

Under an argon atmosphere 3 mL 2 M Na2CO3 solution and 173 mg (0.15 mmol) tetrakis-triphenylphosphane-palladium are added to a solution of 720 mg (3.0 mmol) 4-(5-bromo-pyridin-2-yl)-2-methyl-but-3-yn-2-ol and 593 mg (3.6 mmol) 4-chlorophenyl-boric acid in 60 mL 1,4-dioxane and the reaction mixture is stirred for 18 h at 85° C. The mixture is evaporated down i. vac., the residue is combined with water, extracted exhaustively with EtOAc, the organic phase is washed with water and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, PE/EtOAc 1:1).

Workup

customThe mixture is evaporated down i
extractionextracted exhaustively with EtOAc
washthe organic phase is washed with water
dry with materialdried over Na2SO4
customis purified by chromatography (silica gel, PE/EtOAc 1:1)

Sources & evidence

ORD record: ord-3f069d70169b475c9c67d3df485d8442
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618132B2

Reaction notes

Loading…