5-Bromo-2-methoxypyridine → 5-(3,4-Dimethoxyphenyl)-2-methoxypyridine

HRID 582426

Reaction equation

HRID 582426 reaction equation
C[Sn](C)(C)[C:3]1[CH:4]=[C:5]([O:11][CH3:12])[C:6]([O:9][CH3:10])=[CH:7][CH:8]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20](Br)=[CH:19][N:18]=1>CN(C)C=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>[CH3:12][O:11][C:5]1[CH:4]=[C:3]([C:20]2[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[N:18][CH:19]=2)[CH:8]=[CH:7][C:6]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 27348955-Bromo-2-methoxypyridineHCID 112435354-Trimethylstannylveratrole

Product 1

HCID 187885605-(3,4-Dimethoxyphenyl)-2-methoxypyridine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2.00 g (6.64 mmol) of 4-trimethylstannylveratrole, 2.49 g (13.2 mmol) of 2-methoxy-5-bromopyridine and 370 mg (0.332 mmol) of Pd (PPh3)4 in 30 mL of dry dimethylformamide is flushed thoroughly with nitrogen and heated to 90° C. for 12 hours. The reaction mixture is partitioned between ethyl acetate (150 mL) and water (100 mL). The aqueous layer is back extracted with ethyl acetate (100 mL) and the combined organics are washed with brine (75 mL), dried (MgSO4) and evaporated to give a crude yellow oil. The oil is chromatographed on silica gel (eluting with 95:5 hexane/ethyl acetate and then with 9:1 hexane/ethyl acetate) which gives 5-(3,4-dimethoxy-phenyl)-2-methoxypyridine m.p 83°-84° C.)

Workup

  1. customThe reaction mixture is partitioned between ethyl acetate (150 mL) and water (100 mL)
  2. extractionThe aqueous layer is back extracted with ethyl acetate (100 mL)
  3. washthe combined organics are washed with brine (75 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give a crude yellow oil
  7. customThe oil is chromatographed on silica gel (
  8. washeluting with 95:5 hexane/ethyl acetate

Sources & evidence

ORD record
ord-6888f749710d4c6f9e8edde8202eb394
Source dataset
uspto-grants-1999_07
Patent number
USRE036256

Linked notes

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