7-BROMO-2-METHYL-2H-INDAZOLE

A mixture of 7-bromoindazole (3; 576 mg, 2.92 mmol) and NaOH (510 mg, 12.7 mmol) in 15 mL H2O were heated in an oil bath under N2 atmosphere until the solids dissolved and the resulting solution was cooled to 65° C. Dimethyl sulfate (0.78 mL, 1.03 g, 8.18 mmol) was added and the mixture stirred at 65° for 2 hr. The reaction mixture was cooled to rt and extracted with CH2Cl2 (2.x.50 mL). The combined CH2Cl2 extracts were washed with brine and dried over Na2SO4. Evaporation ofthe solvent afforded 775 mg of a mixture of 1-methyl- and 2-methy-7-bromoindazoles which were separated by flash chromatography on SiO2 using EtOAc:hexane (1:2) which afforded 251 mg (45percent) of 7-bromo-2-methylindazole (4).Example 3 7- (2, 4-Dichloro-phenyl) -2, 3-dimethyl-2H-indazole ; hydrochloride Me Me '-' N-Me-, .. N Br Br Br 6 8 : R' /i '9_ N Ar 7 : R=R'=Me ; Ar 2, 4, 6-trimethylphenyl \ N-MESTEP 1 A solution OF 7-BROMO-LH-INDAZOLE (3; 1.71 g, 8.67 mmol) and dimethyl sulfate (0.90 mL, 9.5 mmol) in 30 mL of toluene was stirred at 110 °C for 4 h, then allowed to cool. The mixture was carefully washed with 30 mL of a saturated aqueous NAHC03 solution, dried over MGS04, filtered (rinsing with diethyl ether), and concentrated to an orange oil Column chromatography (0-50percent EtOAc/hexanes) afforded 7-bromo-2-methyl-2H- indazole (6: R = Me; 1.33 g, 73percent) as a light tan solid.

Molecular Weight:211.06
XLogP3:2.3
Hydrogen Bond Acceptor Count:1
Exact Mass:209.97926
Monoisotopic Mass:209.97926
Topological Polar Surface Area:17.8
Heavy Atom Count:11
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes