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Toluene → 7-Bromo-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17305
Notes
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Reaction equation

HRID 17305 reaction equation
BrC1C(O)=C([C:9]2([C:12](N)=[O:13])[CH2:11][CH2:10]2)C(C#N)=C(C)C=1C1C=CC=CC=1.C1(C(O[C:30]2([NH2:46])[C:35]([C:36]#[N:37])=[C:34]([CH3:38])[C:33]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[C:32]([Br:45])[CH2:31]2)=O)CC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[Br:45][C:32]1[C:33]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[C:34]([CH3:38])[C:35]([C:36]#[N:37])=[C:30]2[C:31]=1[O:13][C:12]([CH:9]1[CH2:11][CH2:10]1)=[N:46]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 86630815(2-Bromo-5-cyano-3-hydroxy-6-methylbiphenyl-4-yl)cyclopropanecarboxamide 4-amino-2-bromo-5-cyano-6-methylbiphenyl-4-yl cyclopropanecarboxylate

Product 1

HCID 685852697-Bromo-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileYield 85.7%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Procedure

Next, a mixture of (2-bromo-5-cyano-3-hydroxy-6-methylbiphenyl-4-yl)cyclopropanecarboxamide/4-amino-2-bromo-5-cyano-6-methylbiphenyl-4-yl cyclopropanecarboxylate mixture (160 mg, 0.426 mmol), p-toluenesulfonic acid monohydrate (24 mg, 0.128 mmol) and toluene (13 ml) was heated under reflux for 1.5 hours. After cooling, the reaction liquid was diluted with ethyl acetate, successively washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine, dried on anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure to obtain a pale brown residue. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to obtain the entitled compound (129 mg) as a colorless solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureAfter cooling
  4. customthe reaction liquid
  5. washsuccessively washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine
  6. dry with materialdried on anhydrous magnesium sulfate
  7. customthe solvent was evaporated away under reduced pressure
  8. customto obtain a pale brown residue
  9. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-0b75770d7e314c74a417b15c56735c91
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737166B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes