Hydrochloric Acid → HCID 86646398, compound

HRID 1877276Notes

Reaction equation

HRID 1877276 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[N:16][CH:17]=2)[S:9][C:10]=1[CH3:11].Cl.O>O1CCCC1>[CH3:19][O:18][C:15]1[N:16]=[CH:17][C:12]([C:8]2[S:9][C:10]([CH3:11])=[C:6]([CH:2]=[O:1])[CH:7]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 68509547HCID 68509547, compound

Product 1

HCID 86646398HCID 86646398, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(5-bromo-2-methylthiophen-3-yl)-1,3-dioxolane (1.7 g), 2-methoxy-5-pyridineboronic acid (1.3 g), tetrakis(triphenylphosphine)palladium(0) (0.4 g), 2N aqueous sodium carbonate solution (10 mL) and 1,2-dimethoxyethane (20 mL) was stirred under reflux overnight under an argon atmosphere. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 30% ethyl acetate/hexane) to give 5-[4-(1,3-dioxolan-2-yl)-5-methylthiophen-2-yl]-2-methoxypyridine as an oil. The obtained 5-[4-(1,3-dioxolan-2-yl)-5-methylthiophen-2-yl]-2-methoxypyridine was dissolved in tetrahydrofuran (10 mL), 1N hydrochloric acid (10 mL) was added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was crystallized from ethyl acetate/hexane to give the title compound (1.2 g, 75%) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-6c36fe0dc9d54753a287a807310f831c
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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