Sodium Hydroxide → HCID 67119555, compound

HRID 2079952Notes

Reaction equation

HRID 2079952 reaction equation
[C:1]([O:3][CH2:4][CH3:5])#[CH:2].[B]1OC2C(=CC=CC=2)O1.[CH3:15][O:16][C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21](Cl)=[N:20][C:19]=1[NH2:25].[OH-].[Na+]>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[CH3:15][O:16][C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([CH:2]=[CH:1][O:3][CH2:4][CH3:5])=[N:20][C:19]=1[NH2:25]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 61239Ether, ethyl ethynylHCID 6327445BenzcatechinboraneHCID 57415887Methyl 2-amino-6-chloronicotinate

Product 1

HCID 67119555HCID 67119555, compoundYield 68.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl ethynyl ether (3.6 g, 25.7 mmol) in tetrahydrofuran (10 mL) was added catechol borane (3.08 g, 25.7 mmol) on an ice bath. Immediately, the cold bath was removed, the reaction mixture was allowed to room temperature, and then, the solution was stirred for 1.5 hours under reflux. This reaction mixture was allowed to room temperature. To this mixture solution were added 2-amino-6-chloro-nicotinic acid methyl ester (1.6 g, 8.57 mmol), sodium hydroxide powder (1.13 g, 28.3 mmol), tetrakis(triphenylphosphine)palladium(0) (0.99 g, 0.857 mmol) and dioxane (20 mL), which was then stirred for 2 hours under reflux. The reaction mixture was allowed to room temperature, and partitioned into water and ethyl acetate. The organic layer was separated, the solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography, and the title compound (1.30 g, 5.85 mmol, 68%) was obtained as a brown solid.

Workup

  1. customImmediately, the cold bath was removed
  2. customwas allowed to room temperature
  3. temperatureunder reflux
  4. customwas allowed to room temperature
  5. stirringwas then stirred for 2 hours
  6. temperatureunder reflux
  7. customwas allowed to room temperature
  8. custompartitioned into water and ethyl acetate
  9. customThe organic layer was separated
  10. customthe solvent was evaporated in vacuo
  11. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-aa04f6188f2f43e58754724e029dda48
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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