Water → Methyl 3-(5-methyl-2-pyridinyl)-5-vinylbenzoate

HRID 1257539Notes

Reaction equation

HRID 1257539 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH:19]([B-](F)(F)F)=[CH2:20].[K+].C(N(CC)CC)C.O>C(O)C.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[CH:9]=[C:4]([CH:3]=[C:2]([CH:19]=[CH2:20])[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[N:13][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 59599704Methyl 3-bromo-5-(5-methylpyridin-2-yl)benzoate

Product 1

HCID 66896192Methyl 3-(5-methyl-2-pyridinyl)-5-vinylbenzoateYield 91.3%

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 702EthanolSolvent

Procedure

To a solution of methyl 3-bromo-5-(5-methylpyridin-2-yl)benzoate (2.0 g, 6.53 mmol) in ethanol (13 mL) was added potassium vinyltrifluoroborate (1.31 g 9.80 mmol), triethylamine (1.37 mL, 9.80 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.267 g, 0.327 mmol). The reaction mixture was stirred and microwaved at 140° C. for 10 min. The reaction mixture was cooled to ambient temperature. Water was added, and ethanol was concentrated. The mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate) gave the title compound (1.51 g). MS 254.1 (M+1).

Workup

  1. custommicrowaved at 140° C. for 10 min
  2. concentrationethanol was concentrated
  3. extractionThe mixture was extracted with dichloromethane (3×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-e5199169a7974be8a2e4086ebd0436fc
Source dataset
uspto-grants-2013_06
Patent number
US08461185B2

Reaction notes

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