Ethyl 2,2,2-triethoxyacetate → Ethyl 6-bromo-4-cyano-7-fluoro-5-methyl-1,3-benzoxazole-2-carboxylate

HRID 17392Notes

Reaction equation

[NH2:1][C:2]1[C:9]([OH:10])=[C:8]([F:11])[C:7]([Br:12])=[C:6]([CH3:13])[C:3]=1[C:4]#[N:5].[CH2:14]([O:16][C:17](OCC)([O:23]CC)[C:18](OCC)=O)[CH3:15]>CCCCCC>[Br:12][C:7]1[C:6]([CH3:13])=[C:3]([C:4]#[N:5])[C:2]2[N:1]=[C:18]([C:17]([O:16][CH2:14][CH3:15])=[O:23])[O:10][C:9]=2[C:8]=1[F:11]

Participants

Conditions

Temperature: 130 °C

Procedure

Under nitrogen atmosphere, a mixture of 2-amino-5-bromo-4-fluoro-3-hydroxy-6-methylbenzonitrile (I-75) (6.67 g, 27.2 mmol) and ethyl triethoxyacetate (24.0 g, 54.4 mmol) was stirred at 130° C. for 15 hours. After cooling, n-hexane was added to the reaction liquid, and the precipitated solid was collected by filtration. The obtained solid was suspended and washed in diethyl ether to obtain the entitled compound (7.10 g, 80%) as a pale dark brown solid.

Workup

temperatureAfter cooling
filtrationthe precipitated solid was collected by filtration
washwashed in diethyl ether

Sources & evidence

ORD record: ord-b781b3d8c25744e5908d183c004c4eaf
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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