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Methyl 4-(3-hydroxy-6-nitroindazol-1-ylmethyl)-3-methoxybenzoate (T) (35.7 g.) was added to a mixture of sodium (2.3 g.) and methanol (200 ml.). The mixture was stirred for 18 hours, and evaporated. The residue was dissolved in N,N-dimethylformamide (100 ml.), cooled to 0° C., and benzyl bromide (15.5 ml.) added. After 18 hours at ambient temperature, ethyl acetate and 1N sodium hydroxide solution were added. The precipitate was isolated by filtration, washed with ether, and chromatographed by HPLC on silica gel, eluting with dichloromethane, to give methyl 4-(3-benzyloxy-6-nitroindazol-1-ylmethyl)-3-methoxybenzoate (CC) (27 g., 60%) as a solid; NMR (250 MHz, DMSO-d6): 3.84(s,3H, OMe); 3.86(s,3H, OMe); 5.38(s,2H, NCH2); 5.65(s,2H, OCH2); 6.95(d,1H); 7.36 (m,3H); 7.46(m,5H); 7.86(m,2H); 8.66(s,1H).

1. customevaporated
2. dissolutionThe residue was dissolved in N,N-dimethylformamide (100 ml.)
3. additionbenzyl bromide (15.5 ml.) added
4. waitAfter 18 hours at ambient temperature
5. additionethyl acetate and 1N sodium hydroxide solution were added
6. customThe precipitate was isolated by filtration
7. washwashed with ether
8. customchromatographed by HPLC on silica gel
9. washeluting with dichloromethane