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ChemicalBook CAS DataBase List 6-BROMO-1-ISOPROPYL-1H-INDAZOLE-4-CARBOXYLIC ACID
1346702-54-2

6-BROMO-1-ISOPROPYL-1H-INDAZOLE-4-CARBOXYLIC ACID synthesis

7synthesis methods
-

Yield:1346702-54-2 94%

Reaction Conditions:

Stage #1: methyl 6-bromo-1-(1-methylethyl)-1H-indazole-4-carboxylatewith water;sodium hydroxide in tetrahydrofuran;methanol at 20; for 3 h;
Stage #2: with hydrogenchloride in water; pH=4 - 5;

Steps:

3.b

b) 6-bromo-l-(l-methylethyl)-l//-indazole-4-carboxylic acidTo a solution of 6-bromo-l-(l-methylethyl)-lH-indazole-4-carboxylate (0.58 g, 1.952 mmol in methanol (12 mL) and tetrahydrofuran (3 mL) was added 3 N NaOH (3.25 mL, 9.76 mmol) via syringe and stirred for 3 h at RT. The volatiles were removed in vacuo then diluted with water and slowly acidifed with 1 N HC1 to pH 4-5. The contents were extracted with 20% THF/EtOAc (3x). The combined organics were washed with brine, dried over MgS04, filtered, and concentrated to give 6-bromo-l-(l-methylethyl)-lH-indazole-4-carboxylic acid (0.52 g, 94 % yield). H NMR (400 MHz, DMSO-i/6) d ppm 13.54 (s, 1 H) 8.36 - 8.43 (m, 2 H) 7.82 (d, J=1.52 Hz, 1 H) 5.11 (quin, J=6.57 Hz, 1 H) 1.48 (s, 3 H) 1.47 (s, 3 H); LC-MS(ES) [M+H]+ 283.4/285.2

References:

WO2011/140325,2011,A1 Location in patent:Page/Page column 41