p-Toluenesulfonic acid → HCID 66620966, compound

HRID 415147Notes

Reaction equation

HRID 415147 reaction equation
[F:1][C:2]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH:19]=[CH:18][C:3]=1[C:4]([NH:6][C:7]1[C:8](O)=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:5].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH:19]=[CH:18][C:3]=1[C:4]1[O:5][C:8]2[C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:14][CH:15]=[CH:16][C:7]=2[N:6]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 66620856HCID 66620856, compound

Product 1

HCID 66620966HCID 66620966, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
118 °C

Procedure

Methyl 3-(2-fluoro-4-(pyridin-2-yl)benzamido)-2-hydroxybenzoate (1.40 g, 3.8 mmol) and 4-methylbenzenesulfonic acid (1.82 g, 9.6 mmol) were added to toluene (50 mL) and the mixture was stirred at 118° C. 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). 500 mg of methyl 2-(2-fluoro-4-(pyridin-2-yl)phenyl)benzo[d]oxazole-7-carboxylate was obtained as a solid; yield 38%. LC-MS (ESI) m/z: 349 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-f5b76fe94e744326ad690f01c7d2a027
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

Loading…