Boron tribromide → HCID 57725645, compound

Temperature

0 °C

To a solution of (S)—N-(1-cyclohexylethyl)-6-methoxybenzo[d]thiazol-2-amine (3.39 g, 10 mmol) in 30 mL of DCM was added 1 M boron tribromide in DCM (20 mL, 20 mmol) slowly at 0° C. The reaction solution was stirred at 0° C. for 20 min and then at room temperature for 2 hours. The reaction mixture was concentrated in vacuo and the residue was dissolved in EtOAc (400 mL) and water (90 mL) and stirred at room temperature for 10 min. To the mixture was added excess solid NaHCO3 until basic. Stirring was continued at room temperature for 1 hour. The separated aqueous layer was extracted with EtOAc (100 mL). The combined organic layers were washed water (50 mL), saturated NaCl solution (50 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel column chromatography with EtOAc/hexanes (3/7) provided the title compound as a solid (2.0 grams). ES/MS m/z 277.1 (MH+).

1. waitat room temperature for 2 hours
2. concentrationThe reaction mixture was concentrated in vacuo
3. dissolutionthe residue was dissolved in EtOAc (400 mL)
4. stirringwater (90 mL) and stirred at room temperature for 10 min
5. additionTo the mixture was added excess solid NaHCO3 until basic
6. stirringStirring
7. waitwas continued at room temperature for 1 hour
8. extractionThe separated aqueous layer was extracted with EtOAc (100 mL)
9. washThe combined organic layers were washed water (50 mL), saturated NaCl solution (50 mL)
10. dry with materialdried over sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure
13. customPurification by silica gel column chromatography with EtOAc/hexanes (3/7)

ORD record

ord-231ee11dea714dc8b4cb07520a40f04b

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08293769B2