Sodium Carbonate → 4-(4-Chloro-2-methoxybenzyl)pyridine

HRID 272743Notes

Reaction equation

HRID 272743 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[O:10][CH3:11].[N:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[Cl:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:15]2[CH:16]=[CH:17][N:12]=[CH:13][CH:14]=2)=[C:4]([O:10][CH3:11])[CH:5]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 223274741-(Bromomethyl)-4-chloro-2-methoxybenzene

Product 1

HCID 692188594-(4-Chloro-2-methoxybenzyl)pyridineYield 34.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 1-bromomethyl-4-chloro-2-methoxy-benzene (50 mg, 0.21 mmol), 4-pyridyl boronic acid (39 mg, 0.32 mmol), Pd(PPh3)4 (24 mg, 0.021 mmol) and 2M Na2CO3 were combined in DME (2 mL), purged with N2, and heated to reflux for 3 hours. The mixture was then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 1:1 hexanes/ethyl acetate to provide 17 mg (33%) of the title compound. MS (ESI) m/e 234 (M+H)+.

Workup

  1. custompurged with N2
  2. temperatureheated
  3. temperatureto reflux for 3 hours
  4. customThe mixture was then partitioned between ethyl acetate and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by flash column chromatography on silica gel with 1:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-090b32f6f7524ba682018f2d47557378
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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