2-(Tributylstannyl)pyrazine → 7-Fluoro-5-methyl-6-phenyl-2-(pyrazin-2-yl)-1,3-benzoxazole-4-carbonitrile

HRID 17472Notes

Reaction equation

C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[N:10][CH:9]=[CH:8][N:7]=1)CCC.C(C1(C)C(O)=C(C(C)(C)C)C=CC1)(C)(C)C.Cl[C:37]1[O:38][C:39]2[C:40](=[C:42]([C:54]#[N:55])[C:43]([CH3:53])=[C:44]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:45]=2[F:46])[N:41]=1>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.C1(C)C=CC=CC=1>[F:46][C:45]1[C:44]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[C:43]([CH3:53])[C:42]([C:54]#[N:55])=[C:40]2[C:39]=1[O:38][C:37]([C:6]1[CH:11]=[N:10][CH:9]=[CH:8][N:7]=1)=[N:41]2

Participants

Conditions

Temperature: 125 °C

Procedure

2-Tri-n-butylstannylpyrazine (409 mg, 1.11 mmol), dichlorobis(triphenylphosphine)palladium(II) (51.9 mg, 0.074 mmol) and 2,6-di-tert-butylcresol (32.6 mg, 0.148 mmol) were added to a toluene (20 ml) solution of 2-chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (212 mg, 0.739 mmol), followed by heating under reflux in an oil bath at 125° C. for 2 hours. The solvent was evaporated away under reduced pressure, then the residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=2:1) to obtain the entitled compound (146 mg, 59.8%) as a colorless solid.

Workup

temperatureby heating
customThe solvent was evaporated away under reduced pressure
customthe residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=2:1)

Sources & evidence

ORD record: ord-ed771845c06c4fa78d84fc0f9e2d67db
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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