Tributylphenyltin → 2-Cyclopropyl-7-methoxy-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17616

Reaction equation

Br[C:2]1[C:3]([O:17][CH3:18])=[C:4]2[O:8][C:7]([CH:9]3[CH2:11][CH2:10]3)=[N:6][C:5]2=[C:12]([C:15]#[N:16])[C:13]=1[CH3:14].C([Sn](CCCC)(CCCC)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)CCC.C(C1(C)C(O)=C(C(C)(C)C)C=CC1)(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>[CH:9]1([C:7]2[O:8][C:4]3[C:5](=[C:12]([C:15]#[N:16])[C:13]([CH3:14])=[C:2]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:3]=3[O:17][CH3:18])[N:6]=2)[CH2:11][CH2:10]1

Participants

Conditions

Temperature: 100 °C

Procedure

Under argon atmosphere, bis(triphenylphosphine)palladium(II) dichloride (777 mg, 1.11 mmol) was added to a 1,4-dioxane (110 ml) solution of 6-bromo-2-cyclopropyl-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrile (I-83) (3.40 g, 11.1 mmol), tributylphenyltin (5.28 g, 14.4 mmol) and 2,6-di-tert-butylcresol (488 mg, 2.21 mmol), followed by stirring in an oil bath at 100° C. for 15 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, and washed with water and saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, and the residue obtained by concentration was washed with diethyl ether to obtain the entitled compound (3.30 g, 98%) as a pale gray solid.

Workup

customThe reaction liquid
concentrationwas concentrated under reduced pressure
dissolutionthe residue was dissolved in ethyl acetate
washwashed with water and saturated brine
dry with materialAfter drying over anhydrous sodium sulfate
customthe insoluble matter was separated by filtration
customthe residue obtained by concentration
washwas washed with diethyl ether

Sources & evidence

ORD record: ord-68507d3cc36e415e80c5a36e8ee390ba
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Linked notes

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