2-Bromo-3-fluoropyridine → 3-Fluoro-2-(2-fluoro-5-nitrophenyl)pyridine

HRID 1061753Notes

Reaction equation

HRID 1061753 reaction equation
Br[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1B1OC(C)(C)C(C)(C)O1>>[F:8][C:7]1[C:2]([C:11]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:10]=2[F:9])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 27628032-Bromo-3-fluoropyridineHCID 38332972-Fluoro-5-nitrophenylboronic acid, pinacol ester

Product 1

HCID 222853393-Fluoro-2-(2-fluoro-5-nitrophenyl)pyridine

Procedure

2-Bromo-3-fluoropyridine, prepared according to the procedure of Queguiner et al. in Tetrahedron, 1983, 39, 2009-21, was coupled with 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (as prepared in Example 2, part a)) by the method of Example 2, part b) to yield 3-fluoro-2-(2-fluoro-5-nitrophenyl)pyridine, which was transformed into 2-(5-bromo-2-fluorophenyl)-3-fluoropyridine by the method of Example 4, parts b) and c). This was converted into 4-fluoro-3-(3-fluoropyridin-2-yl)phenylboronic acid by the method of Example 5 part d), using bis(neopentyl glycolato)diboron instead of bis(pinacolato)diboron. δH (400 MHz, DMSO) 8.58 (1H, m), 8.19 (2H, s), 8.04 (1H, dd, J 8 and 2), 7.95 (1H, m), 7.86 (1H, m), 7.57 (1H, m), 7.31 (1H, dd, J 11 and 8).

Workup

  1. customas prepared in Example 2, part a)) by the method of Example 2, part b)

Sources & evidence

ORD record
ord-451a9e9817bc4df88133ce1afe87d52e
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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