2′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile → 5'-[7-Acetyl-[1,8]naphthyridin-4-yl]-2'-fluorobiphenyl-2-carbonitrile

HRID 1061843Notes

Reaction equation

HRID 1061843 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](=[O:14])[CH3:13])=[N:7]2.[F:15][C:16]1[CH:21]=[CH:20][C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18][C:17]=1[C:31]1[C:32]([C:37]#[N:38])=[CH:33][CH:34]=[CH:35][CH:36]=1>>[C:12]([C:6]1[N:7]=[C:8]2[C:3]([C:2]([C:19]3[CH:20]=[CH:21][C:16]([F:15])=[C:17]([C:31]4[C:32]([C:37]#[N:38])=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:18]=3)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:5]=1)(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 117716472′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrileHCID 222853341-(5-chloro-1,8-naphthyridin-2-yl)Ethanone

Product 1

HCID 99254355'-[7-Acetyl-[1,8]naphthyridin-4-yl]-2'-fluorobiphenyl-2-carbonitrileYield 83%

Procedure

This was prepared in 83% yield from 1-(5-chloro-[1,8]naphthyridin-2-yl)ethanone (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) 2.97 (3H, s), 7.45 (1H, t, J 9.0), 7.55 (1H, td, J 7.4, 1.2), 7.58-7.62 (4H, m), 7.71 (1H, td, J 7.4, 1.2), 7.84 (1H, dd, J 7.8, 0.8), 8.26 (1H, d, J 8.6), 8.59 (1H, d, J 8.6), 9.26 (1H, d, J 4.3). m/z (ES+) 368 [MH]+.

Sources & evidence

ORD record
ord-1e1f470dab88405faea3784f4b33b00f
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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