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Reagents and conditions: (i) R2Br, K2CO3, DMF, 60 °C, 4–16 h; (ii) 7 M NH3 in MeOH, RT to 90 °C, 16 h to 2 d; (iii) 10% Pd/C, H2 (g), EtOH, 60–75 °C, 16 h; (iv) 4-fluorobenzoic acid, TEA, PyBrop, DCE, MW 120 °C, 20 min; (v) KOtBu, iPrOH, MW 130 °C, 30 min; (vi) cat. DMF, (COCl)2, DCM, 0 °C, 1 h, then RT, 2 h; (vii) MeOH, 0 °C, 30 min; (viii) BBr3, DCM, −78 °C to RT, 16 h; (ix) CH3OCO(CH2)2Br, K2CO3, DMF, 60 °C, 16 h.
