Potassium Phosphate, Tribasic → Methyl 6-(1,4-dioxaspiro[4,5]dec-7-en-8-yl)nicotinate

HRID 2042741Notes

Reaction equation

HRID 2042741 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[O:12]1[C:16]2([CH2:21][CH2:20][C:19](B(O)O)=[CH:18][CH2:17]2)[O:15][CH2:14][CH2:13]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[O:12]1[C:16]2([CH2:21][CH2:20][C:19]([C:2]3[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=3)=[CH:18][CH2:17]2)[O:15][CH2:14][CH2:13]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 13349623Methyl 6-bromopyridine-3-carboxylateHCID 441187651,4-Dioxaspiro[4.5]dec-7-en-8-ylboronic acid

Product 1

HCID 69059497Methyl 6-(1,4-dioxaspiro[4,5]dec-7-en-8-yl)nicotinate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 6-bromonicotinate (2.11 g, 9.78 mmol), 1,4-dioxaspiro[4,5]dec-7-en-8-ylboronic acid (2 g, 10.86 mmol), palladium(II) acetate (109 mg, 0.48 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.40 g, 0.97 mmol) and potassium phosphate (6.2 g, 29.1 mmol) were placed in a Schlenk tube and the tube was placed under vacuum and filled with argon. Dioxane (30 mL) and water (4 mL) were added and the tube was heated (80° C.) overnight. The mixture was partitioned with ether and water and the organic phase was washed with brine, dried (magnesium sulfate), filtered and evaporated. The residue was purified by silica gel chromatography using 30% ethyl acetate in hexanes to provide the title compound as a slightly yellow oil, which solidified upon standing.

Workup

  1. additionfilled with argon
  2. customThe mixture was partitioned with ether and water
  3. washthe organic phase was washed with brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b5b69c7f5ff94a33a8dd16512a5f676e
Source dataset
uspto-grants-2013_11
Patent number
US08586594B2

Reaction notes

Loading…