1H-Indole-7-carboxylic acid, 4-broMo-, Methyl ester

1H-Indole-7-carboxylic acid, 4-broMo-, Methyl ester Property

Boiling point:

402.3±25.0 °C(Predicted)

Density 

1.629±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

14.49±0.30(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C10H8BrNO2/c1-14-10(13)7-2-3-8(11)6-4-5-12-9(6)7/h2-5,12H,1H3

InChIKey

JTBLJEGYYYHKGQ-UHFFFAOYSA-N

SMILES

N1C2=C(C(Br)=CC=C2C(OC)=O)C=C1

Safety

HS Code 

2933998090

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

P271Use only outdoors or in a well-ventilated area.

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

1H-Indole-7-carboxylic acid, 4-broMo-, Methyl ester Chemical Properties,Usage,Production

Uses

Methyl 4-bromo-1H-indole-7-carboxylate can be used as a pharmaceutical synthesis intermediate. It can be prepared by reacting methyl 4-bromo-2-nitrobenzoic acid with vinyl magnesium bromide.

Synthesis

GENERAL STEPS: To a solution of 4-bromo-1H-indole-7-carboxylic acid (33 g, 137 mmol) in N,N-dimethylformamide (DMF, 300 mL) was added cesium carbonate (Cs2CO3, 90 g, 276 mmol) and stirred at room temperature for 1 hour. Subsequently, iodomethane (29.3 g, 206 mmol) was added slowly and dropwise at 0 °C. The reaction mixture was gradually warmed up to room temperature and stirring was continued for 3 hours. After completion of the reaction, the mixture was poured into water and extracted with ethyl acetate (EtOAc, 200 mL x 2). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford methyl 4-bromo-1H-indole-7-carboxylate (13.8 g, 20% yield). The structure of the product was confirmed by 1H NMR (CDCl3): δ 9.98 (s, 1H), 7.76-7.74 (d, J = 8 Hz, 1H), 7.39-7.34 (m, 2H), 6.68-6.66 (m, 1H), 4.00 (s, 3H).

References

[1] Patent: WO2014/210255, 2014, A1. Location in patent: Page/Page column 95