1,2-Dichloroethane → HCID 59316740, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 4-{4-[(hydroxyamino)(imino)methyl]-2H-indazol-2-yl}butanoate & ethyl 4-{4-[(hydroxyamino)(imino)methyl]-1H-indazol-1-yl}butanoate (D56) (0.27 g, 0.930 mmol) (a 3:2 mix of 1 and 2-isomers), 3-chloro-4-[(1-methylethyl)oxy]benzoic acid (D3) (0.200 g, 0.930 mmol), EDC (0.196 g, 1.023 mmol) and HOBT (0.157 g, 1.023 mmol) in N,N-dimethylformamide (5 ml) was stirred at 80° C. for 16 hrs then at 120° C. for 2 hours. The reaction was cooled, diluted with ethyl acetate (40 ml) and water (40 ml) and the organic washed with 3×15 ml of water, dried (magnesium sulphate) and evaporated. The crude material was purified by flash chromatography eluting with 3:7 ethyl acetate/hexane to give two products which were triturated with 1:1 ether/hexane to give 66 mgs of upper spot and 36 mgs of lower. The upper spot was the desired 1-substituted indazole. δH (CDCl3, 400 MHz): 1.24 (3H, t), 1.46 (6H, d), 2.31 (4H, m), 4.12 (2H, q), 4.55 (2H, t), 4.73 (1H, m), 7.08 (1H, d), 7.52 (1H, dd), 7.62 (1H, d), 8.07 (1H, dd), 8.11 (1H, dd), 8.29 (1H, d), 8.70 (1H, d).

Provenance & Evidence