2′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile → HCID 10200567, compound

HRID 1061814Notes

Reaction equation

HRID 1061814 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:22]=[CH:21][C:20](B2OC(C)(C)C(C)(C)O2)=[CH:19][C:18]=1[C:32]1[C:33]([C:38]#[N:39])=[CH:34][CH:35]=[CH:36][CH:37]=1>>[F:16][C:17]1[CH:22]=[CH:21][C:20]([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:19][C:18]=1[C:32]1[C:33]([C:38]#[N:39])=[CH:34][CH:35]=[CH:36][CH:37]=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 222852765-chloro-2-(trifluoromethyl)-1,8-Naphthyridine

Product 1

HCID 10200567HCID 10200567, compoundYield 66%

Procedure

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol) was coupled to 2′-fluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile (prepared as described in Example 2, steps a) to e), 90 mg, 0.28 mmol) as described in Example 7 part g), affording 2′-fluoro-5′-(7-trifluoromethyl[1,8]naphthyridin-4-yl)biphenyl-2-carbonitrile (56 mg, 66%). δH (360 MHz, CDCl3) 7.47 (1H, t, J 9.3), 7.53-7.62 (5H, m), 7.71 (1H, td, J, 7.7 and 1.4), 7.85 (1H, dd, J 7.7 and 0.7), 7.88 (1H, d, J 8.4), 8.71 (1H, d, J 8.8), 9.28 (1H, d, J 4.6). m/z (ES+) 394 [MH]+.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-e54b643efee8491382df0713e35e3054
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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