2,6-Di-tert-butyl-4-methylphenol → tert-Butyl [3-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)cyclopent-2-enyl]carbamate

HRID 17306

Reaction equation

HRID 17306 reaction equation
Br[C:2]1[C:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:4]([CH3:16])[C:5]([C:14]#[N:15])=[C:6]2[C:10]=1[O:9][C:8]([CH:11]1[CH2:13][CH2:12]1)=[N:7]2.[C:23]([O:27][C:28]([NH:30][CH:31]1[CH2:35][CH2:34][C:33]([Sn](CCCC)(CCCC)CCCC)=[CH:32]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].C(C1C(O)=C(C(C)(C)C)C=C(C)C=1)(C)(C)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[C:14]([C:5]1[C:6]2[N:7]=[C:8]([CH:11]3[CH2:12][CH2:13]3)[O:9][C:10]=2[C:2]([C:33]2[CH2:34][CH2:35][CH:31]([NH:30][C:28](=[O:29])[O:27][C:23]([CH3:25])([CH3:24])[CH3:26])[CH:32]=2)=[C:3]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:4]=1[CH3:16])#[N:15]

Participants

6

Reactant 3

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 15630117Tert-butyl (3-tri-n-butylstannylcyclopent-2-enyl)carbamateHCID 685852697-Bromo-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 86630817tert-Butyl [3-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)cyclopent-2-enyl]carbamateYield 75.8%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A 1,4-dioxane (6 ml) solution of 7-bromo-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-46) (89 mg, 0.252 mmol), 1-(N-tert-butoxycarbonylamino)-3-tri-n-butylstannyl-2-cyclopentene (143 mg, 0.302 mmol), bis(triphenylphosphine)palladium(II) chloride (8.8 mg, 0.0126 mmol), 2,6-di-tert-butyl-p-cresol (5.6 mg, 0.0252 mmol) was refluxed overnight. After cooling, the reaction liquid was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1→8:1→5:1) to obtain the entitled compound (87 mg, 75%) as a pale brown solid.

Workup

  1. temperatureAfter cooling
  2. customthe reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1→8:1→5:1)

Sources & evidence

ORD record
ord-3a82d942589f41e3916fd6f225c1caf5
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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