p-Toluenesulfonic acid → HCID 67258003, compound

HRID 1619387Notes

Reaction equation

HRID 1619387 reaction equation
[O:1]=[C:2]1[C:6](=[CH:7][O-])[CH2:5][CH2:4][O:3]1.[Na+].[Br:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[CH:12]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O>[Br:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]([NH:17][CH:7]=[C:6]2[CH2:5][CH2:4][O:3][C:2]2=[O:1])[CH:12]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6932822-Amino-4-bromopyridineHCID 66632760HCID 66632760, compound

Product 1

HCID 67258003HCID 67258003, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of sodium (2-oxodihydrofuran-3(2H)-ylidene)methano-late (134 mg, 1 mmol), 4-bromopyridin-2-amine (173 mg, 1.0 mmol) and 4-methylbenzenesulfonic acid (50 mg, 0.29 mmol) in toluene was stirred at 150° C. for 1 hr. After the suspension was diluted with water, the solution was adjusted to pH 8 and extracted with ethyl acetate. Then, the organic layers were dried over Na2SO4 and concentrated to give crude product, which was used for then next reaction without further purification. MS (ESI): 269, 271 (MH+).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThen, the organic layers were dried over Na2SO4
  3. concentrationconcentrated
  4. customto give crude product, which
  5. customnext reaction
  6. customwithout further purification

Sources & evidence

ORD record
ord-f046496710a246a6977b564887f5d03f
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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