Sodium Carbonate → HCID 67997029, compound

HRID 45778Notes

Reaction equation

HRID 45778 reaction equation
Br[C:2]1[C:3]([S:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:4][CH:5]=[CH:6][CH:7]=1.CC1(C)C(C)(C)OB([C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]([C:35]#[N:36])=[CH:27][CH:26]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[C:35]([C:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:25]([C:2]2[C:3]([S:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:4][CH:5]=[CH:6][CH:7]=2)=[CH:26][CH:27]=1)#[N:36]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 67997086Ethyl 2-(3-bromopyridin-2-ylthio)-2-methylpropanoateHCID 679975564-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthonitrile

Product 1

HCID 67997029HCID 67997029, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 2-(3-bromopyridin-2-ylthio)-2-methylpropanoate (271 mg, 0.89 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthonitrile (248 mg, 0.89 mmol), palladium tetrakis triphenylphoshine (51 mg, 0.044 mmol) and aqueous sodium carbonate solution (2M, 1.5 mL, 3 mmol) in dioxane (3 mL) was degassed and heated to 80° C. for 5 hours. The mixture was washed with water and extracted with ethyl acetate. The organic layer was dried with Mg2SO4, concentrated and purified by chromatography to yield ethyl 2-(3-(4-cyanonaphthalen-1-yl)pyridin-2-ylthio)-2-methylpropanoate (0.121 g, 36%).

Workup

  1. customwas degassed
  2. washThe mixture was washed with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried with Mg2SO4
  5. concentrationconcentrated
  6. custompurified by chromatography

Sources & evidence

ORD record
ord-fa70e52026254c75ba967e3aee38eb32
Source dataset
uspto-grants-2013_09
Patent number
US08541589B2

Reaction notes

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