p-Toluenesulfonic acid → Methyl 2-(3-(pyridin-2-yl)phenyl)benzo[d]oxazole-7-carboxylate

HRID 415292Notes

Reaction equation

HRID 415292 reaction equation
O[C:2]1[C:11]([NH:12][C:13](=[O:26])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[CH:15]=2)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:16]1[CH:15]=[C:14]([C:13]2[O:26][C:2]3[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=[CH:10][C:11]=3[N:12]=2)[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 66621343Methyl 2-hydroxy-3-(3-(pyridin-2-yl)benzamido)benzoate

Product 1

HCID 66621080Methyl 2-(3-(pyridin-2-yl)phenyl)benzo[d]oxazole-7-carboxylateYield 20%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 2-hydroxy-3-(3-(pyridin-2-yl)benzamido)benzoate (1.4 g, 4 mmol) and 4-methylbenzenesulfonic acid (1.9 g, 10 mmol) were added to toluene (30 mL) and the mixture was stirred under reflux for 2 days. The resulting mixture was extracted with ethyl acetate (100 mL×4) and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1 to 10:1). 264 mg of methyl 2-(3-(pyridin-2-yl)phenyl)benzo[d]oxazole-7-carboxylate as a solid was obtained, yield: 20%. LC-MS (ESI) m/z: 331 (M+1)+.

Workup

  1. temperatureunder reflux for 2 days
  2. extractionThe resulting mixture was extracted with ethyl acetate (100 mL×4)
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1 to 10:1)

Sources & evidence

ORD record
ord-39aaa46eb4544b149f4ed6e6fd03c1e7
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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