Cesium carbonate → 2-Cyclopropyl-7-fluoro-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrile

HRID 17338

Reaction equation

Br[CH2:2][C:3]([C:5]1[C:6]([F:20])=[C:7]2[O:11][C:10]([CH:12]3[CH2:14][CH2:13]3)=[N:9][C:8]2=[C:15]([C:18]#[N:19])[C:16]=1[CH3:17])=O.C(=O)([O-])[O-].[Cs+].[Cs+].[C:27]([NH2:30])(=[S:29])[CH3:28]>C1(C)C=CC=CC=1>[CH:12]1([C:10]2[O:11][C:7]3[C:8](=[C:15]([C:18]#[N:19])[C:16]([CH3:17])=[C:5]([C:3]4[N:30]=[C:27]([CH3:28])[S:29][CH:2]=4)[C:6]=3[F:20])[N:9]=2)[CH2:14][CH2:13]1

Participants

Conditions

Temperature: 100 °C

Procedure

6-(2-Bromoacetyl)-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-79) (39.98 g, 28.6 mmol) was dissolved in toluene (270 ml), then cesium carbonate (13.02 g, 39.90 mmol) and thioacetamide (2.58 g, 34.28 mmol) were added, followed by stirring at 100° C. for 6 hours under nitrogen atmosphere. The reaction liquid was cooled, the insoluble matter was separated by filtration through Celite, ethyl acetate was added to the filtrate, followed by washing with water and saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was recrystallized and purified with n-hexane/ethyl acetate to obtain the entitled compound (3.96 g, 44%) as a white solid.

Workup

customThe reaction liquid
temperaturewas cooled
customthe insoluble matter was separated by filtration through Celite, ethyl acetate
additionwas added to the filtrate
washby washing with water and saturated brine
dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
customthe solvent was evaporated away under reduced pressure
customThe resulting residue was recrystallized
custompurified with n-hexane/ethyl acetate

Sources & evidence

ORD record: ord-f02d5e1c41b3406881161b6fbf955e13
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Linked notes

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