HCID 22240089, compound → HCID 10271521, compound

HRID 1061779Notes

Reaction equation

HRID 1061779 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[C:22]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=[C:21]([F:29])[CH:20]=[CH:19][C:18]=1B(O)O>>[F:29][C:21]1[C:22]([C:23]2[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=2)=[C:17]([F:16])[CH:18]=[CH:19][C:20]=1[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

Participants

3

Reactant 2

HCID 22240089HCID 22240089, compoundHCID 222852765-chloro-2-(trifluoromethyl)-1,8-Naphthyridine

Product 1

HCID 10271521HCID 10271521, compoundYield 36%

Procedure

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol) was coupled to 2,4-difluoro-3-(pyridin-4-yl)benzeneboronic acid (66 mg, 0.28 mmol) as described in Example 7 part g), affording 5-(2,4-difluoro-3-pyridin-4-ylphenyl)-2-trifluoromethyl-[1,8]naphthyridine (30 mg, 36%). δH (360 MHz, CDCl3) 7.29 (1H, m), 7.41-7.50 (3H, m), 7.62 (1H, d, J 4.6), 7.85 (1H, d, J 8.8), 8.33 (1H, dd, J 2.3 and 8.6), 8.75-8.77 (2H, m), 9.34 (1H, d, J 4.6). m/z (ES+) 388 [MH]+.

Sources & evidence

ORD record
ord-46801d7a0bcf4bc5b266d5aaf20fe6d4
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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