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ChemicalBook CAS DataBase List 1-N-BOC-6-METHOXY-3-METHYL-1H-INDAZOLE

1-N-BOC-6-METHOXY-3-METHYL-1H-INDAZOLE synthesis

2synthesis methods
-

Yield:691900-70-6 59%

Reaction Conditions:

with dmap;triethylamine in acetonitrile at 0 - 20;

Steps:

35 EXAMPLE 35: 1-[(tert-butoxycarbonyl)oxy]-6-methoxy-3-methyl-1H-indazole

EXAMPLE 35: 1-[(tert-butoxycarbonyl)oxy]-6-methoxy-3-methyl-1H-indazole Di-tert-butyl-dicarbonate in acetonitrile was mixed at 0°C with 6-methoxy-3-methyl-1H-indazole (prepared following the procedure described by F. Dennler, Tetrahedron, 22, 1966, 3131-3139) (26.27 g, 0.162 mol), acetonitrile (200 ml), triethylamine (25 ml, 0.178 mol), DMAP (3.96 g, 0.0324 mol). The mixture was stirred at room temperature overnight. Acetonitrile was concentrated under vacuum. The mixture was extracted with ethylacetate and acidified at pH = 2 with a solution of concentrated HCl, dried over Na2SO4, filtered and put in diisopropylether. 23.9 g of the expected product were obtained (as solid, 59 %). 1H-NMR (DMSO d6): 1.60 (s, 9H), 2.44 (s, 3H), 3.85 (s, 3H), 6.95 (dd, 1H), 7.50 (d, 1H), 7.65 (d, 1H).

References:

EP1647549,2006,A1 Location in patent:Page/Page column 19