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. Author manuscript; available in PMC: 2021 May 6.
Published in final edited form as: Org Biomol Chem. 2020 May 6;18(17):3288–3296. doi: 10.1039/c9ob02682g

Scheme 2.

Scheme 2.

Synthesis of 5-fluoronaphthylsulfonamides (a) i) HBF4 (aq) NaNO2 ii) molten KHF2 (2–20%) (b) HNO3, NaNO2 (60%) (c) BnOH, NaH, CH2Cl2 (61%) (d) Pt/C, NaBH4 (99%) (e) CsF, DMSO, 100 °C (23%) (f) NH3, TBHP, NaOH, THF (70%) (g) BnBr, Cs2CO3, CH2Cl2 (75%) (h) i) Pt/C, NaBH4 ii) 4-methoxybenzenesulfonyl chloride, pyridine, MgSO4 (62%) (i) Pd/C, H2, (j) PhI(OAc)2, PhSH, (CF3)2CHOH (37%) (k) MeI, K2CO3, DMF (84%) (l) i) Pd/C, NaBH4 ii) R2SO2Cl, pyridine, MgSO4 (45–89%) (m) Br2, CH2Cl2 (56–75%)