Sodium Carbonate → HCID 22662095, compound

HRID 392871Notes

Reaction equation

HRID 392871 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]2[CH3:14])[N:3]=1.[CH2:15]([O:22][C:23]1[C:28]([CH2:29][CH3:30])=[CH:27][C:26](B(O)O)=[C:25]([O:34][CH3:35])[CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)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>[CH2:15]([O:22][C:23]1[C:28]([CH2:29][CH3:30])=[CH:27][C:26]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([N:8]3[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]3[CH3:14])[N:3]=2)=[C:25]([O:34][CH3:35])[CH:24]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 155127672-Bromo-6-(2,5-dimethyl-1H-pyrrol-1-yl)pyridineHCID 22662103HCID 22662103, compound

Product 1

HCID 22662095HCID 22662095, compoundYield 73.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere, 5.00 g (19.91 mmol) of 2-bromo-6-(2,5-dimethylpyrrol-1-yl)pyridine, 5.98 g (20.91 mmol) of 4-benzyloxy-5-ethyl-2-methoxy-phenylboronic acid (5), 8.44 g (79.64 mmol) of sodium carbonate and 1.15 g (0.996 mmol) of tetrakis(triphenylphosphine)palladium(0) were combined in 90 mL of ethanol and 10 mL of water. The solution was allowed to reflux for 64 hours, and then the reaction mixture was concentrated in vacuo. The resultant yellow residue was partitioned between ethyl acetate (200 mL) and water (200 mL). The aqueous layer was extracted again with ethyl acetate (200 mL). The combined organic extracts were washed with brine (1×200 mL), dried over sodium sulfate, filtered and concentrated in vacuo to yield crude product as a yellow oil which crystallized upon standing. Recrystallization of this solid from absolute ethanol afforded 6.00 g (73%) of 2-(4-benzyloxy-5-ethyl-2-methoxy-phenyl)-6-(2,5-dimethyl-pyrrol-1-yl)-pyridine (6) as a tan solid.

Workup

  1. temperatureto reflux for 64 hours
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe resultant yellow residue was partitioned between ethyl acetate (200 mL) and water (200 mL)
  4. extractionThe aqueous layer was extracted again with ethyl acetate (200 mL)
  5. washThe combined organic extracts were washed with brine (1×200 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto yield crude product as a yellow oil which
  10. customcrystallized
  11. customRecrystallization of this solid from absolute ethanol

Sources & evidence

ORD record
ord-27d71911b317411e8157e7892752fd53
Source dataset
uspto-grants-2004_10
Patent number
US06803470B2

Reaction notes

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