Sodium Bicarbonate → Methyl 3-bromo-5-(5-methylpyridin-2-yl)benzoate

HRID 888392Notes

Reaction equation

HRID 888392 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](I)[CH:7]=[C:6]([Br:11])[CH:5]=1.[Br-].[CH3:14][C:15]1[CH:16]=[CH:17][C:18]([Zn+])=[N:19][CH:20]=1.C(=O)(O)[O-].[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>[Br:11][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([C:18]2[CH:17]=[CH:16][C:15]([CH3:14])=[CH:20][N:19]=2)[CH:7]=1)[C:3]([O:2][CH3:1])=[O:12]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 21942573Methyl 3-bromo-5-iodobenzoateHCID 178427808HCID 178427808, compound

Product 1

HCID 59599704Methyl 3-bromo-5-(5-methylpyridin-2-yl)benzoate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution methyl-3-bromo-5-iodobenzoate (10.0 g, 29.3 mmol) and 5-methyl-2-pyridylzinc bromide (0.5 M in THF; 64.5 mL, 32.3 mmol) in tetrahydrofuran (84 mL) was added tetrakis(triphenylphosphine)palladium(0) (1.70 g, 1.47 mmol). The reaction mixture was stirred at ambient temperature. After 6 h, saturated aqueous sodium bicarbonate was added. The mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with sodium potassium tartrate tetrahydrate (2×), brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→95% dichloromethane/ethyl acetate) gave the title compound. MS 306.0 (M).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×)
  2. washThe combined organic extracts were washed with sodium potassium tartrate tetrahydrate (2×), brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (100% dichloromethane→95% dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-61015c0bdfa84b43bb6acd7aed8cc341
Source dataset
uspto-grants-2012_08
Patent number
US08247401B2

Reaction notes

Loading…