(5-iodo-2-methoxyphenyl)methanamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 67 (500 mg, 1.9 mmol) and ammonium acetate (1.5 g, 19.4 mmol) in dry methanol (6 mL) NaCNBH3 (170 mg, 2.66 mmol) was added in one portion. The resulting mixture was stirred at room temperature for 48 h. Concentrated HCl was added until pH<2. The methanol was evaporated and the resulting white residue was dissolved in water (10 mL) and washed with Et2O (2×10 mL). The aqueous phase was then basified with aqueous KOH (45%), saturated with NaCl and extracted with CH2Cl2 (10 mL×4). The combined organic phases were dried over Na2SO4, filtered and concentrated to give 68 as a yellow oil (200 mg, 40%). 1H NMR (CDCl3, 300 MHz) δ 7.55-7.45 (m, 2H), 6.46-6.58 (m, 1H), 3.82-3.72 (m, 5H), 1.63 (br s, 2H). MS (m/e) (positive FAB) 264.1 (M+H)+, m.p. 95-97° C. The methanol was evaporated the resulting white residue was dissolved in water (10 mL) washed with Et2O (2×10 mL) extracted with CH2Cl2 (10 mL×4) The combined organic phases were dried over Na2SO4 filtered concentrated