Benzylamine → HCID 67021195, compound

Participants

Reaction Conditions

Reaction Steps

Fifty-seven milligrams (57 mg; 0.1 mmol) of 3-[3-(2-(4-chloro-2-fluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-yl)-phenoxymethyl]-benzoic acid methyl ester (prepared similarly to that of 4-[4-(2-benzyl-7-trifluoromethyl-2H-indazol-3-yl)-phenoxymethyl]-benzoic acid methyl ester in preparation of Example 2) were dissolved in 2 ml of dry THF followed by the addition of 110 μl of benzylamine (1 mmol). The reaction mixture was cooled to −30° C. and 450 μl of 2M solution of butylmagnesiumbromide in ether were added dropwise. Then the reaction mixture was stirred for 30 min at −30° C. and left overnight at 0° C. The reaction mixture was quenched with aq NH4Cl solution and product was extracted with EtOAc. Flash column chromatography (SiO2, dichloromethane as an eluant) afforded N-benzyl-3-({3-[2-(4-chloro-2-fluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-yl]phenoxy}methyl)benzamide in 66% yleld.

Provenance & Evidence