Water → HCID 86692512, compound

HRID 1748566Notes

Reaction equation

HRID 1748566 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:17])[C:5]([C:8]2(C(O)=O)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.O>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:17])[C:5]([CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 962WaterHCID 86692511HCID 86692511, compound

Product 1

HCID 86692512HCID 86692512, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4-(5-bromo-3-methylpyridin-2-yl)tetrahydro-2H-pyran-4-carboxylic acid (420 mg) in dimethylsulfoxide (1 ml) was stirred at 150° C. for 1.5 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added thereto, and extracted with chloroform. The organic layer was washed with water and saturated brine sequentially, then dried over anhydrous sodium sulfate, and the solvent was evaporated. The obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give the titled compound (316 mg) as a white solid. MS (ESI) m/z: 256, 258 (M+H)+.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water and saturated brine sequentially
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThe obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b4ba8f8339a44ed397218c7b2c647938
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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