Sodium Carbonate → HCID 86725417, compound

HRID 1503886Notes

Reaction equation

HRID 1503886 reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[C:17]([Cl:24])=[C:18](N)[CH:19]=[CH:20][C:21]=1Br)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC1(C)C(C)(C)OB([C:33]2[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH:34]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O>[C:1]([O:5][C:6]([N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:16]1[CH:21]=[CH:20][C:19]([C:33]2[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:43])([CH3:44])[CH3:45])=[O:40])[CH2:35][CH:34]=2)=[CH:18][C:17]=1[Cl:24])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 86725418HCID 86725418, compound

Product 1

HCID 86725417HCID 86725417, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the product of Example 60A (380 mg, 1.23 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (380 mg, 1.23 mmol) and sodium carbonate (391 mg, 3.69 mmol) in 1,4-dioxane (8 mL) and water (2 mL) was degassed and heated at 80° C. for 16 hours. After cooling to ambient temperature and concentration, the residue was partitioned between ethyl acetate and water and the aqueous layer was extracted with ethyl acetate (3×35 mL). The combined organic phase was washed with saturated brine, dried over sodium carbonate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 8/1 petroleum/ethyl acetate to provide the title compound.

Workup

  1. customwas degassed
  2. temperatureAfter cooling to ambient temperature
  3. concentrationconcentration
  4. customthe residue was partitioned between ethyl acetate and water
  5. extractionthe aqueous layer was extracted with ethyl acetate (3×35 mL)
  6. washThe combined organic phase was washed with saturated brine
  7. dry with materialdried over sodium carbonate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography on silica gel (200-300 mesh)
  11. washeluting with 8/1 petroleum/ethyl acetate

Sources & evidence

ORD record
ord-266f6741c028495ba4fc93e522647d70
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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