p-Toluenesulfonic acid monohydrate → methyl 2-(1H-indol-2-yl)benzo[d]oxazole-7-carboxylate

HRID 415232Notes

Reaction equation

HRID 415232 reaction equation
O[C:2]1[C:11]([NH:12][C:13]([C:15]2[NH:16][C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].O.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[NH:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[C:15]1[C:13]1[O:14][C:2]2[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=[CH:10][C:11]=2[N:12]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 66621063methyl 2-hydroxy-3-(1H-indole-2-carboxamido)benzoate

Product 1

HCID 66621353methyl 2-(1H-indol-2-yl)benzo[d]oxazole-7-carboxylateYield 47.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Methyl 2-hydroxy-3-(1H-indole-2-carboxamido)benzoate (170 mg, 0.5 mmol) and 4-methylbenzenesulfonic acid monohydrate (400 mg, 4.0 mmol) were added to xylene (10 mL) and the mixture was stirred at reflux for 10 hr. The resulting mixture was extracted with dichloromethane (100 mL×4) and concentrated. Then the crude product was purified by column chromatography (silica gel, petroleum ether:ethyl acetate 20:1) to obtain methyl 2-(1H-indol-2-yl)benzo[d]oxazole-7-carboxylate as a solid (70 mg, yield 43%). LC-MS (ESI) m/z 293 [M+1]+.

Workup

  1. temperatureat reflux for 10 hr
  2. extractionThe resulting mixture was extracted with dichloromethane (100 mL×4)
  3. concentrationconcentrated
  4. customThen the crude product was purified by column chromatography (silica gel, petroleum ether:ethyl acetate 20:1)

Sources & evidence

ORD record
ord-265943e5258e45a3926411e78a3993e5
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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