2′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile → HCID 10136133, compound

HRID 1061841Notes

Reaction equation

HRID 1061841 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[S:13][CH:14]=[CH:15][N:16]=1)=[N:7]2.[F:17][C:18]1[CH:23]=[CH:22][C:21](B2OC(C)(C)C(C)(C)O2)=[CH:20][C:19]=1[C:33]1[C:34]([C:39]#[N:40])=[CH:35][CH:36]=[CH:37][CH:38]=1>>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[C:3]3[C:8](=[N:7][C:6]([C:12]4[S:13][CH:14]=[CH:15][N:16]=4)=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)=[CH:20][C:19]=1[C:33]1[C:34]([C:39]#[N:40])=[CH:35][CH:36]=[CH:37][CH:38]=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 22285275HCID 22285275, compound

Product 1

HCID 10136133HCID 10136133, compoundYield 59%

Procedure

This was prepared in 59% yield from 5-chloro-2-(thiazol-2-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) 7.45 (1H, t, J 9.0), 7.51 (1H, d, J 4.3), 7.54 (1H, td, J 7.4, 1.2), 7.58 (1H, d, J 3.1), 7.60-7.63 (3H, m), 7.71 (1H, td, J 7.4, 1.2), 7.84 (1H, dd, J 7.4, 1.2), 8.02 (1H, d, J 3.1), 8.48 (1H, d, J 8.6), 8.54 (1H, d, J 8.6), 9.46 (1H, d, J 4.7). m/z (ES+) 409 [MH]+.

Sources & evidence

ORD record
ord-2199b6ad43ed498092999f1b1d1abfd6
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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