2′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile → HCID 10201108, compound

HRID 1061840Notes

Reaction equation

HRID 1061840 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[N:7]2.[F:18][C:19]1[CH:24]=[CH:23][C:22](B2OC(C)(C)C(C)(C)O2)=[CH:21][C:20]=1[C:34]1[C:35]([C:40]#[N:41])=[CH:36][CH:37]=[CH:38][CH:39]=1>>[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[C:3]3[C:8](=[N:7][C:6]([C:12]4[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=4)=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)=[CH:21][C:20]=1[C:34]1[C:35]([C:40]#[N:41])=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

3

Reactant 2

HCID 117716472′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrileHCID 22285337HCID 22285337, compound

Product 1

HCID 10201108HCID 10201108, compoundYield 88%

Procedure

This was prepared in 88% yield from 5-chloro-2-(pyridin-3-yl)-[1,8]naphthyridine (from step a) and 2′-fluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile (from Example 2, step e) using a similar procedure to that described in Example 55, step a. δH (400 MHz, CDCl3) 7.44-7.52 (3H, m), 7.55 (1H, td, J 7.4, 1.2), 7.61-7.65 (3H, m), 7.71 (1H, td, J 7.4, 1.2), 7.85 (1H, dd, J 7.8, 1.2), 8.06 (1H, d, J 9.0), 8.59 (1H, d, J 8.6), 8.71-8.75 (2H, m), 9.20 (1H, d, J 4.7), 9.46 (1H, d, J 1.6). m/z (ES+) 403 [MH]+.

Sources & evidence

ORD record
ord-666256001a3f435c976527279a11879d
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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