Benzene, 1-bromo-4-(trifluoromethyl)- → HCID 68291725, compound

Participants

Reaction Conditions

Reaction Steps

To a vial charged with (4-isopropoxy-3-methyl-phenyl)-[10-(methoxymethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]methanone (30.0 mg, 0.08 mmol), 1-bromo-4-(trifluoromethyl)benzene (19.7 mg, 0.088 mmol), Pd2(dba)3 (23 mg, 0.04 mmol), rac-BINAP (24.8 mg, 0.04 mmol) and sodium tert-butoxide (9.8 mg, 0.088 mmol) were added N-methyl-2-pyrrolidone (0.2 mL) and toluene (1.0 mL). The reaction mixture was heated at 100° C. under nitrogen 18 h. The reaction mixture was cooled to room temperature, filtered and purified via HPLC (1-90% CH3CN/5 mM HCl) to provide (4-isopropoxy-3-methylphenyl)(2-(methoxymethyl)-4-(4-(trifluoromethyl)phenyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methanone (5.0 mg, 0.0077 mmol, 10%). ESI-MS m/z calc. 520.2549. Found 521.3 (M+1)+; Retention time: 2.21 minutes (3 min run).

Provenance & Evidence