2-Fluoro-5-nitrophenylboronic acid, pinacol ester → 3-Fluoro-5-(2-fluoro-5-nitrophenyl)pyridine

HRID 2184065Notes

Reaction equation

HRID 2184065 reaction equation
[F:1][C:2]1[CH:3]=[C:4](OS(C(F)(F)F)(=O)=O)[CH:5]=[N:6][CH:7]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=1B1OC(C)(C)C(C)(C)O1>>[F:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:18]2[CH:19]=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=[CH:22][C:17]=2[F:16])[CH:3]=1

Participants

3

Reactant 2

HCID 38332972-Fluoro-5-nitrophenylboronic acid, pinacol esterHCID 11413882Methanesulfonic acid, trifluoro-, 5-fluoro-3-pyridinyl ester

Product 1

HCID 224735443-Fluoro-5-(2-fluoro-5-nitrophenyl)pyridine

Procedure

Trifluoromethanesulfonic acid 5-fluoropyridin-3-yl ester was coupled with 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane as described in Example 1 to give 3-fluoro-5-(2-fluoro-5-nitrophenyl)pyridine as a white solid: δH (360 MHz, CDCl3) 7.39 (1H, t, J 9), 7.65 (1H, m), 8.31-8.36 (1H, m), 8.42 (1H, dd, J 7 and 3), 8.58 (1H, d, J 3), 8.67 (1H, d, J 1).

Sources & evidence

ORD record
ord-8eea8c0f10ed4f6e9683fe1cbaafc44f
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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