tert-butyl 5-bromoindoline-1-carboxylate Chemical Properties

Melting point:

126-128°C

Boiling point:

363℃

Density 

1.400

Flash point:

173℃

storage temp. 

2-8°C

form 

Solid

pka

-0.02±0.20(Predicted)

color 

White

CAS DataBase Reference

261732-38-1

Safety Information

Hazard Codes 

T,N

Risk Statements 

25-36/37/38-50/53

Safety Statements 

26-45-60-61

RIDADR 

UN2811 - class 6.1 - PG 3 - EHS - Toxic solids, organic, n.o.s., HI: all

WGK Germany 

3

HazardClass 

6.1

HS Code 

2933998090

tert-butyl 5-bromoindoline-1-carboxylate Usage And Synthesis

Chemical Properties

White Solid

Uses

tert-Butyl 5-bromoindoline-1-carboxylate is a brominated indoline derivative and a product of biocatalyzed halogenation of nucleobase analogs. It is used in the synthetic preparation of biologic ally active compounds such as selective human β3 adrenergic receptor agonists.

Synthesis

To a solution of 5-bromo-2,3-dihydro-1H-indole (2.11 g, 10.7 mmol) in tetrahydrofuran (THF, 40 mL) was added di-tert-butyl dicarbonate (Boc2O, 2.56 g, 11.7 mmol). The reaction mixture was stirred at room temperature for 18 hours. After completion of the reaction, the mixture was concentrated under reduced pressure. Purification of the residue by fast column chromatography (eluent: hexane solution of 8% ethyl acetate) afforded tert-butyl 5-bromo-2,3-dihydro-1H-indole-1-carboxylate (2.59 g, 95% yield) as a white solid; mass spectrometry (MS) showed the molecular ion peak (M + H)+ m/z = 298.

References

[1] Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3892 - 3909
[2] Patent: US2008/45543, 2008, A1. Location in patent: Page/Page column 28
[3] Patent: US6534535, 2003, B1
[4] Patent: WO2012/103806, 2012, A1. Location in patent: Page/Page column 47
[5] Patent: WO2016/86200, 2016, A1. Location in patent: Page/Page column 300

tert-butyl 5-bromoindoline-1-carboxylate(261732-38-1)Related Product Information

• TERT-BUTYL 5-BROMOISOINDOLINE-2-CARBOXYLATE
• tert-Butyl 7-bromoheptanoate
• Benzoic acid, 5-bromo-2-[[(1,1-dimethylethoxy)carbonyl]amino]- (9CI)
• tert-Butyl 7-chloro-1H-indole-1-carboxylate
• N-(BOC)-6-fluoro-indole
• N-BOC-6-METHOXYINDOLE
• Hexanoic acid, 6-bromo-, 1,1-dimethylethyl ester
• tert-butyl 5-oxo-L-prolinate
• tert-butyl(7-oxoheptyl) carbamate
• 5-BROMOPENTANOIC ACID, T-BUTYL ESTER
• TERT-BUTYL 6-IODOHEXYLCARBAMATE
• tert-Butyl 9-aminononanoate
• tert-Butyl 5-iodopentylcarbamate
• 3-Boc-6-oxa-3-aza-bicyclo[3.1.0]hexane
• 4-Methoxy-1H-indole-1-carboxylic acid tert-butyl ester
• tert-butyl 4-nitrosopiperazine-1-carboxylate
• tert-Butyl 6-oxohexylcarbamate
• tert-Butyl 8-oxooctylcarbamate