2-Bromoanisole → Tert-butyl 4-(2-methoxyphenyl)-1,4-diazepane-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To 1.6 g (7.99 mmol) [1,4]diazepane-1-carboxylic acid tert-butyl ester was added 1.09 mL (1.64 g, 8.79 mmol) of 2-bromoanisole, 37 mg (0.04 mmol) of Pd2dba3, 75 mg (0.12 mmol) of (±)-BINAP, 1.08 g (11.19 mmol) of NaOt-Bu, 20 mL of toluene and resulting slurry was heated to 80° C. for 20 h. After cooling to 23° C., the reaction mixture was filtered through Celite and evaporated to leave a dark brown oil. Flash chromatography on silica gel, eluting with CH2Cl2/EtOAc (1/0 to 40/1 to 20/1) gave 2.17 g (7.08 mmol, an 89% yield) of the title compound as a light yellow oil. 1H NMR (300 MHz, CDCl3): δ1.45 and 1.47 (singlets, 9H—rotational isomers), 1.91-2.07 (m, 2H), 3.16-3.31 (m, 4H), 3.47-3.65 (m, 4H), 3.85 (s, 3H), 6.72-6.96 (m, 4H); IR (KBr, cm−1):1691s; MS (ES) m/z (relative intensity): 307 (M++H, 100). Anal. Calcd. for C17H26N2O3: C, 66.64; H, 8.55; N, 9.14. Found: C, 66.18; H 8.54; N, 8.80.

Provenance & Evidence