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

HRID 17470

Reaction equation

C([Sn](CCCC)(CCCC)[C:6]1[S:7][CH:8]=[CH:9][N:10]=1)CCC.C(C1(C)C(O)=C(C(C)(C)C)C=CC1)(C)(C)C.Cl[C:36]1[O:37][C:38]2[C:39](=[C:41]([C:53]#[N:54])[C:42]([CH3:52])=[C:43]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:44]=2[F:45])[N:40]=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:45][C:44]1[C:43]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[C:42]([CH3:52])[C:41]([C:53]#[N:54])=[C:39]2[C:38]=1[O:37][C:36]([C:6]1[S:7][CH:8]=[CH:9][N:10]=1)=[N:40]2

Participants

Conditions

Temperature: 125 °C

Procedure

2-Tri-n-butylstannylthiazole (392 mg, 1.05 mmol), dichlorobis(triphenylphosphine)palladium(II) (49.0 mg, 0.070 mmol) and 2,6-di-tert-butylcresol (30.7 mg, 0.14 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) (200 mg, 0.698 mmol), followed by heating under reflux in an oil bath at 125° C. for 5 hours in an argon atmosphere. The solvent was evaporated away under reduced pressure, then the residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=9:1→2:1) to obtain the entitled compound (70.0 mg, 29.9%) as a pale yellow 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=9:1→2:1)

Sources & evidence

ORD record: ord-0047f5e8ceb241b98ab3b2476aa0cd4c
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Linked notes

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