5-bromo-1-naphthamide(SALTDATA: FREE) synthesis

Yield:22531-59-5 97%

Reaction Conditions:

Stage #1: 5-bromo-1-naphthalenecarboxylic acidwith thionyl chloride at 85; for 2 h;
Stage #2: with ammonium hydroxide in tetrahydrofuran at 0 - 20; for 2 h;

Steps:

Synthesis of compound 10-e

5-Bromo-1-naphthoic acid (980mg, 3.92mmol) was added to thionyl chloride (5mL).
The mixture was stirred at 85°C for 2hrs, concentrated under reduced pressure.
The residue was dissolved in anhydrous THF (10mL), the solution was added dropwise into 25%-28% aqueous ammonia (20mL) at 0°C.
The mixture was warmed to room temperature and further stirred for 2hrs, followed by being extracted with EA (60mL*3).
The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give white solid 10-e (950mg, yield 97%).
The product was used directly for the next step without further purification. LC-MS (ESI): m/z = 250 [M+H]⁺.

References:

EP3275867,2018,A1 Location in patent:Paragraph 0138; 0139