1-Boc-3-(4-BroMo-1H-pyrazol-1-yl)azetidine

1-Boc-3-(4-BroMo-1H-pyrazol-1-yl)azetidine Property

storage temp. 

2-8°C

form 

solid

Appearance

White to off-white Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

1-Boc-3-(4-BroMo-1H-pyrazol-1-yl)azetidine Chemical Properties,Usage,Production

Synthesis

N-Boc-3-methylsulfonyloxyazetidine (304 mg, 1.21 mmol), 4-bromopyrazole (178 mg, 1.21 mmol), a mineral oil suspension of 60% NaH (73 mg, 1.82 mmol), and 2 mL of DMF were added to the microwave tube.The reaction mixture was microwaved at 110 °C for 30 min. Upon completion of the reaction, the mixture was partitioned between EtOAc (200 mL) and saturated NaHCO3 solution (2 × 50 mL) and washed with brine (50 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give 360 mg of the yellow oily product tert-butyl 3-(4-bromo-1H-pyrazol-1-yl)azetidine-1-carboxylate in 98% yield.1H NMR (400 MHz, DMSO-D6) δ ppm 1.36-1.43 (m, 9H), 4.08 (s, 2H), 4.18- 4.31 (m, 2H), 5.12-5.22 (m, 1H), 7.67 (s, 1H), 8.14 (s, 1H).

References

[1] Patent: US2006/46991, 2006, A1. Location in patent: Page/Page column 57-58
[2] Patent: WO2006/21881, 2006, A2. Location in patent: Page/Page column 62-63; 64
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 18, p. 6342 - 6363