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Reagents and conditions: (i) cat. DMF, (COCl)2, DCM, 0 °C, 1 h, then RT, 2 h; (ii) CH3NH2, 0 °C to RT, 6 h, 88% over two steps; (iii) 10% Pd/C, H2 (g), EtOH, 75 °C, 18 h, 85%; (iv) 4-fluorobenzoic acid, TEA, PyBrop, DCE, MW 120 °C, 20 min; (v) KOtBu, iPrOH, MW 130 °C; (vi) 4-fluorobenzaldehyde, I2, DMF, 80 °C, 16 h, 59%.
