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

HRID 1061785Notes

Reaction equation

HRID 1061785 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]([F:15])([F:14])[F:13])=[N:7]2.[F:16][C:17]1[CH:18]=[C:19]([C:32]2[C:33]([C:38]#[N:39])=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:20]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:22]=1>>[F:16][C:17]1[CH:18]=[C:19]([C:32]2[C:33]([C:38]#[N:39])=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:20]=[C:21]([C:2]2[C:3]3[C:8](=[N:7][C:6]([C:12]([F:15])([F:14])[F:13])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)[CH:22]=1

Participants

3

Reactant 2

HCID 116742013'-Fluoro-5'-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrileHCID 222852765-chloro-2-(trifluoromethyl)-1,8-Naphthyridine

Product 1

HCID 101573813'-Fluoro-5'-(7-trifluoromethyl[1,8]naphthyridin-4-yl)biphenyl-2-carbonitrileYield 35%

Procedure

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol) was coupled to 3′-fluoro-5′-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile (90 mg, 0.28 mmol) as described in Example 7 part g), affording 3′-fluoro-5′-(7-trifluoromethyl[1,8]naphthyridin-4-yl)biphenyl-2-carbonitrile (30 mg, 35%). δH (360 MHz, CDCl3) 7.32-7.36 (1H, m), 7.41-7.44 (1H, m), 7.50-7.59 (3H, m), 7.64 (1H, d, J 4.6), 7.72 (1H, td, J 7.7 and 1.4), 7.85 (1H, dd, J 7.7 and 0.7), 7.90 (1H, d, J 8.8), 8.75 (1H, d, J 8.8), 9.30 (1H, d, J 4.2). m/z (ES+) 394 [MH]+.

Sources & evidence

ORD record
ord-b0b3d5f46a40404bab03a0311ac2a9d7
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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