HCID 11593861, compound → HCID 10110735, compound

HRID 1061754Notes

Reaction equation

HRID 1061754 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](B(O)O)=[CH:19][C:18]=1[C:26]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][N:27]=1>>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:11]=[CH:10][N:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][C:6]([C:12]([F:15])([F:14])[F:13])=[N:7]3)=[CH:19][C:18]=1[C:26]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][N:27]=1

Participants

3

Reactant 2

HCID 11593861HCID 11593861, compoundHCID 222852765-chloro-2-(trifluoromethyl)-1,8-Naphthyridine

Product 1

HCID 10110735HCID 10110735, compoundYield 49.2%

Procedure

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (100 mg, 0.43 mmol) was coupled to 4-fluoro-3-(3-fluoropyridin-2-yl)phenylboronic acid (131 mg, 0.56 mmol) as described in Example 3 part g), affording 5-[4-fluoro-3-(3-fluoropyridin-2-yl)phenyl]-2-trifluoromethyl[1,8]-naphthyridine (82 mg, 49%). δH (360 MHz, CDCl3) 7.39-7.44 (2H, m), 7.55-7.63 (3H, m), 7.79 (1H, dd, J 2.3 and 6.5), 7.85 (1H, d, J 8.4), 8.55-8.60 (2H, m), 9.28 (1H, d, J 4.6). m/z (ES+) 388 [MH]+.

Sources & evidence

ORD record
ord-f971c73cfdb94f96988ba2d62384ab43
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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