4-Bromopyridine → HCID 9948724, compound

HRID 1005957Notes

Reaction equation

HRID 1005957 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][S:7][C:8]1[NH:9][C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=1.Br[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1.[OH-].[K+].C1OCCOCCOCCOCCOCCOC1>O.CS(C)=O>[N:21]1[CH:22]=[CH:23][C:18]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][S:7][C:8]2[NH:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[N:9]=2)=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 142684-BromopyridineHCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 22675463HCID 22675463, compound

Product 1

HCID 9948724HCID 9948724, compoundYield 31.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

0.47 g of the compound obtained in Example 13a, 0.30 g of 4-bromo-pyridine, 0.80 g of KOH and 0.20 g of 18-crown-6-ether were added to 20 ml of dimethyl sulfoxide and heated to 150° C. for 8 hours. The reaction mixture was cooled, then added with water and extracted with ethyl acetate. The extract was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate) to obtain 0.19 g of the title compound (yield: 30%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-ef19cbf496f54f12a5fc449206a1343f
Source dataset
uspto-grants-2004_09
Patent number
US06787561B1

Reaction notes

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