Sodium Carbonate → 4-(2,6-Dimethylpyridin-3-yl)-1-naphthoic acid

HRID 352362Notes

Reaction equation

HRID 352362 reaction equation
[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](B(O)O)=[CH:6][CH:5]=1)([OH:3])=[O:2].Cl.Br[C:19]1[C:20]([CH3:26])=[N:21][C:22]([CH3:25])=[CH:23][CH:24]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.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>[CH3:26][C:20]1[C:19]([C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=2)=[CH:24][CH:23]=[C:22]([CH3:25])[N:21]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 227118323-Bromo-2,6-dimethylpyridine hydrochlorideHCID 227118634-Carboxynaphthalene-1-boronic acid

Product 1

HCID 227118694-(2,6-Dimethylpyridin-3-yl)-1-naphthoic acid

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

A stirred mixture of D17 (0.32 g, 1.5 mmole), 3-bromo-2,6-dimethylpyridine hydrochloride (Synthesis 1974, 4, 293; 0.37 g, 1.6 mmole), Na2CO3 (0.48 g, 5.6 mmole) and tetrakis(triphenylphosphine)palladium (0) (0.08 g, 0.07 mmole) in 50% DME/water (20 ml) was heated at reflux under argon for 18 h. The mixture was concentrated in vacuo to 50% volume, diluted with water (20 ml), washed with EtOAc (2×10 ml), acidified with 2M HCl to pH 4 and extracted with DCM (3×25 ml). The combined extract was dried and evaporated to dryness. The residue was triturated in Et2O to afford the title compound as a buff powder (0.29 g, 69%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under argon for 18 h
  3. concentrationThe mixture was concentrated in vacuo to 50% volume
  4. additiondiluted with water (20 ml)
  5. washwashed with EtOAc (2×10 ml)
  6. extractionextracted with DCM (3×25 ml)
  7. extractionThe combined extract
  8. customwas dried
  9. customevaporated to dryness
  10. customThe residue was triturated in Et2O

Sources & evidence

ORD record
ord-8088deaf56fa4d98b0f6bc2ff50d1433
Source dataset
uspto-grants-2004_06
Patent number
US06747030B1

Reaction notes

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