Triethylamine → HCID 67520320, compound

HRID 1925323Notes

Reaction equation

HRID 1925323 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=[CH:5]2.[CH3:16][O:17][C:18]1[N:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:16][O:17][C:18]1[N:23]=[CH:22][C:21]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=[CH:5]3)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 11367671Methyl 6-hydroxy-1-naphthoate

Product 1

HCID 67520320HCID 67520320, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution/suspension of methyl 6-hydroxy-1-naphthoate (2.49 g, 12.3 mmol), 6-methoxypyridin-3-ylboronic acid (2.26 g, 14.8 mmol), copper acetate (2.46 g, 13.6 mmol), triethylamine (6.24 g, 61.7 mmol) and 4Å molecular sieves (2.00 g) in acetonitrile (120 mL) was stirred at RT for 16 h. The solids were filtered off. The filtrate was concentrated in vacuo. Water was added and extracted with EtOAc. The organic layer was washed with 1M aqueous NaOH solution, water, brine and dried over Na2SO4, filtered and concentrated in vacuo. Purification by silica gel chromatography afforded the title compound.

Workup

  1. filtrationThe solids were filtered off
  2. concentrationThe filtrate was concentrated in vacuo
  3. additionWater was added
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with 1M aqueous NaOH solution, water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-c80ea3c4489d4ef2a9f9581744c7b143
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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