5-chloro-2-(trifluoromethyl)-1,8-Naphthyridine → HCID 9924825, compound

HRID 1061803Notes

Reaction equation

HRID 1061803 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.CC1(C)COB([C:23]2[CH:24]=[C:25]([C:29]3[N:30]=[N:31][N:32]([CH3:34])[N:33]=3)[CH:26]=[CH:27][CH:28]=2)OC1>>[CH3:34][N:32]1[N:31]=[N:30][C:29]([C:25]2[CH:26]=[C:27]([C:2]3[CH:11]=[CH:10][N:9]=[C:8]4[C:3]=3[CH:4]=[CH:5][C:6]([C:12]([F:15])([F:14])[F:13])=[N:7]4)[CH:28]=[CH:23][CH:24]=2)=[N:33]1

Participants

3

Reactant 2

HCID 222852765-chloro-2-(trifluoromethyl)-1,8-NaphthyridineHCID 22285324HCID 22285324, compound

Product 1

HCID 9924825HCID 9924825, compoundYield 7%

Procedure

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol) was coupled to 5-[3-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)phenyl]-2-methyl-2H-tetrazole (76 mg, 0.28 mmol) as described in Example 7 part g), affording 5-[3-(2-methyl-2H-tetrazol-5-yl)phenyl]-2-trifluoromethyl[1,8]naphthyridine (5 mg, 7%). δH (360 MHz, CDCl3) 4.43 (3H, s), 7.59-7.65 (2H, m), 7.73 (1H, t, J 7.7), 7.83 (1H, d, J 8.4), 8.29 (1H, s), 8.34 (1H, d, J 7.4), 8.56 (1H, d, J 8.1), 9.30 (1H, d, J 3.9). m/z (ES+) 357 [MH]+.

Sources & evidence

ORD record
ord-d182f090882d4923a0be726a2d6590eb
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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