4-Bromoindoline Chemical Properties

Boiling point:

278.8±29.0 °C(Predicted)

Density 

1.514±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

4.20±0.20(Predicted)

form 

liquid

color 

Brown to reddish brown

InChI

InChI=1S/C8H8BrN/c9-7-2-1-3-8-6(7)4-5-10-8/h1-3,10H,4-5H2

InChIKey

YCJCSDSXVHEBRU-UHFFFAOYSA-N

SMILES

N1C2=C(C(Br)=CC=C2)CC1

Safety Information

HS Code 

2933998090

4-Bromoindoline Usage And Synthesis

Chemical Properties

Pale-yellow to Yellow to Brown Liquid

Uses

4-Bromoindoline is a simple active pharmaceutical building block that can be used as a basic skeleton for the preparation of the migraine drug Sumatriptan.

Synthesis

Step 1. 4-Bromoindole (5.00 mL, 39.9 mmol) was dissolved in a solvent mixture of acetic acid (5.00 mL, 87.9 mmol) and methanol (25.0 mL, 617 mmol) and the reaction system was cooled to 0°C. Sodium cyanoborohydride (7.52 g, 0.120 mol) was slowly added under stirring, followed by a slow warming of the reaction mixture to room temperature over 1 hour. After completion of the reaction, the mixture was concentrated and neutralized with saturated aqueous sodium bicarbonate solution. Extraction was carried out using ether and ethyl acetate, the organic phases were combined and washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give 4.11 g (52% yield) of 4-bromo-2,3-dihydro-1H-indole.

References

[1] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2462 - 2471
[2] Patent: US2007/265258, 2007, A1. Location in patent: Page/Page column 24
[3] Patent: WO2007/100880, 2007, A1. Location in patent: Page/Page column 81
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 166 - 178
[5] Organic Letters, 2013, vol. 15, # 22, p. 5662 - 5665

4-Bromoindoline(86626-38-2)Related Product Information

• 4-BROMOISATIN
• 4-BROMOOXINDOLE
• 4-Bromo-5-methyl-2,3-indolinedione
• 4-BROMO-7-METHYLISATIN
• 4-Bromoindoline
• 4-BROMO-5-CHLOROINDOLINE-2,3-DIONE
• 4,6-DIBROMO ISATIN
• 4-BROMO-2,3-DIHYDRO-INDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• 4-bromo-1-(3-chloropropyl)-2,3-dihydro-1H-indole-2,3-dione
• N-BOC-4-BROMOISATIN
• 3-amino-4-bromo-1,3-dihydro-2H-indol-2-one
• 4-bromo-3-(ethylamino)-1,3-dihydro-2H-indol-2-one
• 4-bromo-3-[(2-furylmethyl)amino]-1,3-dihydro-2H-indol-2-one
• 4-bromo-3-(methylamino)-1,3-dihydro-2H-indol-2-one
• 4-bromo-1-(2-chloroprop-2-en-1-yl)-2,3-dihydro-1H-indole-2,3-dione
• 4-bromo-3-(propylamino)-1,3-dihydro-2H-indol-2-one
• (4-bromo-2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetic acid
• 2-[(4-bromo-2-oxo-2,3-dihydro-1H-indol-3-yl)amino]acetamide