2′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile → HCID 10180354, compound

HRID 1061839Notes

Reaction equation

HRID 1061839 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:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])=[N:7]2.[F:19][C:20]1[CH:25]=[CH:24][C:23](B2OC(C)(C)C(C)(C)O2)=[CH:22][C:21]=1[C:35]1[C:36]([C:41]#[N:42])=[CH:37][CH:38]=[CH:39][CH:40]=1>>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[C:3]3[C:8](=[N:7][C:6]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[F:18])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)=[CH:22][C:21]=1[C:35]1[C:36]([C:41]#[N:42])=[CH:37][CH:38]=[CH:39][CH:40]=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 22285307HCID 22285307, compound

Product 1

HCID 10180354HCID 10180354, compoundYield 62%

Procedure

This was prepared in 62% yield from 5-chloro-2-(2-fluorophenyl)-[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 step a. δH (400 MHz, CDCl3) 7.20 (1H, ddd, J 11.7, 8.2 and 1.2), 7.34 (1H, td, J 7.4, 1.2), 7.42-7.48 (2H, m), 7.50 (1H, d, J 4.3), 7.54 (1H, td, J 7.4, 1.2), 7.60-7.65 (3H, m), 7.71 (1H, td, J 7.4, 1.2), 7.84 (1H, dd, J 7.8, 0.8), 8.09 (1H, dd, J 8.6 and 2.3), 8.42 (1H, td, J 7.8, 2.0), 8.49 (1H, d, J 8.6), 9.18 (1H, d, J 4.7). m/z (ES+) 420 [MH]+.

Sources & evidence

ORD record
ord-fc0e375905ff4b55a836f6679a3d34d7
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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