1,2-Dimethoxyethane → Methyl 4-(6-methoxy-3-pyridinyl)benzoate

HRID 1785812Notes

Reaction equation

HRID 1785812 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C[C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[C:13]([C:20]([OH:22])=[O:21])[CH:12]=1.[F-].[Cs+].[CH3:25]OCCOC>CO.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>[CH3:9][O:8][C:5]1[N:6]=[CH:7][C:2]([C:16]2[CH:15]=[CH:14][C:13]([C:20]([O:22][CH3:25])=[O:21])=[CH:12][CH:11]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 25953Cesium fluorideHCID 27348955-Bromo-2-methoxypyridineHCID 22730486HCID 22730486, compound

Product 1

HCID 4674260Methyl 4-(6-methoxy-3-pyridinyl)benzoate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-bromo-2-methoxypyridine (2.93 g, 10 mmol), 4-methylcarboxybenzeneboronic acid (1.80 g, 10 mmol), Pd(Ph3P)4 (0.346 g, 0.3 mmnol) and CsF (1.52 g, 10 mmol) in DME (60 mL) and methanol (30 mL) was heated to reflux for 18 hours and concentrated. The concentrate was dissolved in water (50 mL) and ethyl acetate (300 mL) and the organic phase was washed with water (2×50 mL) and brine (50 mL), dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 3:1 hexanes/ethyl acetate to provide the desired product. MS (APCI) m/e 278, 280 (M−H)−, (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours
  3. concentrationconcentrated
  4. dissolutionThe concentrate was dissolved in water (50 mL)
  5. washethyl acetate (300 mL) and the organic phase was washed with water (2×50 mL) and brine (50 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe concentrate was purified by flash column chromatography on silica gel with 3:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-8d5e1d35e069445ca7eb275c12948410
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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