4-Bromo-2-indolecarboxylic acid

Production Example 30 PRODUCTION EXAMPLE 30 To a solution of compound 1 (0.36 g, 1.49 mmol, 1 eq) and compound 1A (366.33 mg, 1.49 mmol, 1 eq) in DMF (10 mL) was added HATU (851.82 mg, 2.24 mmol, 1.5 eq), DIEA (579.07 mg, 4.48 mmol, 780.41 uL, 3 eq) stirred at 15C for 16 hrs. LCMS showed the starting material was consumed and the desired MS was detected. The reaction was triturated with water (20 mL) and filtered. The filter cake was triturated with EtOAc (20 mL) and filtered. The filter cake was concentrated to give compound 2 (0.5 g, 1.07 mmol, 71.64% yield) as a yellow solid, which was confirmed. The residue was used directly next step without purification. LCMS: RT = 1.345 min, MS cal.: 467.32, [M+H] + = 468.7. 1H NMR (400MHz, DMSO-d6) d ppm 12.06 (s, 1H), 9.23 (s, 1H), 7.54 - 7.44 (m, 3H), 7.43 - 7.36 (m, 3H), 7.30 (d, J = 6.8 Hz, 1H), 7.17 - 7.10 (m, 1H), 6.72 (d, J = 2.0 Hz, 1H), 4.38 - 4.20 (m, 2H), 3.57 (br s, 2H), 2.14 - 1.96 (m, 2H), 1.89 (br d, J = 13.2 Hz, 2H).(7) in the flask to adding the mass ratio of 6:33: 1 of step (6) the obtained 4 - bromo indole -2 - carboxylic acid, THF, to stir until completely dissolved is added after the step (3) the resulting sodium aluminum hydride, reflux reaction for 5 hours and then cooled to 0 C, water quenching after suction filtration, the cake is washed with ethyl acetate, the filtrate is extracted with ethyl acetate, the combined organic layer after washing with saturated sodium chloride solution, dried with anhydrous sodium sulfate, after concentration ethyl acetate by recrystallization to obtain 4 - bromo -2 - hydroxy indole.

Molecular Weight:240.05
XLogP3:3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:238.95819
Monoisotopic Mass:238.95819
Topological Polar Surface Area:53.1
Heavy Atom Count:13
Complexity:222
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes