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924287-65-0

924287-65-0 Structure

924287-65-0 Structure
IdentificationBack Directory
[Name]

Methyl 2-bromo-4-fluorobenzo[d]thiazole-6-carboxylate
[CAS]

924287-65-0
[Synonyms]

Methyl 2-bromo-4-fluorobenzo[d]thiazole-6-carboxylate
methyl 2-bromo-4-fluoro-1,3-benzothiazole-6-carboxylate
6-Benzothiazolecarboxylic acid, 2-bromo-4-fluoro-, methyl ester
[Molecular Formula]

C9H5BrFNO2S
[MDL Number]

MFCD23705964
[MOL File]

924287-65-0.mol
[Molecular Weight]

290.11
Chemical PropertiesBack Directory
[Boiling point ]

378.3±52.0 °C(Predicted)
[density ]

1.763±0.06 g/cm3(Predicted)
[storage temp. ]

under inert gas (nitrogen or Argon) at 2-8°C
[pka]

-2.90±0.10(Predicted)
[Appearance]

Light yellow to yellow Solid
Spectrum DetailBack Directory
[Spectrum Detail]

Methyl 2-bromo-4-fluorobenzo[d]thiazole-6-carboxylate(924287-65-0)1HNMR
Methyl 2-bromo-4-fluorobenzo[d]thiazole-6-carboxylate(924287-65-0)19FNMR
Hazard InformationBack Directory
[Synthesis]

6-Benzothiazolecarboxylic acid, 2-aMino-4-fluoro-, Methyl ester

924287-64-9

Methyl 2-bromo-4-fluorobenzo[d]thiazole-6-carboxylate

924287-65-0

General procedure for the synthesis of methyl 2-bromo-4-fluorobenzo[d]thiazole-6-carboxylate from methyl 2-bromo-4-fluorobenzo[d]thiazole-6-carboxylate: t-BuONO (1.65 g, 16.0 mmol) was slowly added dropwise to a solution of CuBr2 (2.7 g, 12 mmol) in CH3CN (30 mL) at 0 °C, followed by a single addition of 2-amino methyl -4-fluorobenzo[d]thiazole-6-carboxylate (1.8 g, 8.0 mmol). The reaction mixture was stirred at room temperature for 4 h. After completion of the reaction, the reaction mixture was diluted with EtOAc and water. The organic and aqueous layers were separated and the aqueous layer was further extracted with EtOAc. All organic layers were combined, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give methyl 2-bromo-4-fluorobenzo[d]thiazole-6-carboxylate (2.0 g, 86% yield) as a yellow solid. Mass spectrometry (ES+) analysis: the theoretical value of C10H8BrNO3S was 289 and the measured value was 290 [M+H]+.

[References]

[1] Patent: WO2018/81276, 2018, A1. Location in patent: Page/Page column 155
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 24, p. 9960 - 9973
[3] Patent: WO2007/16392, 2007, A2. Location in patent: Page/Page column 35; 48-49
[4] Patent: WO2012/87519, 2012, A1. Location in patent: Page/Page column 84; 85; 86
[5] Patent: WO2012/87520, 2012, A1. Location in patent: Page/Page column 43; 44
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