5-chloro-2-(trifluoromethyl)-1,8-Naphthyridine → HCID 10199830, compound

HRID 1061806Notes

Reaction equation

HRID 1061806 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]([CH:34]=[CH:35][CH:36]=2)[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)OC1>>[N:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[CH2:27][O:26][C:25]1[CH:34]=[C:35]([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:36]=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 222852765-chloro-2-(trifluoromethyl)-1,8-NaphthyridineHCID 22285278HCID 22285278, compound

Product 1

HCID 10199830HCID 10199830, compoundYield 42.9%

Procedure

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol) was coupled to 2-[3-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)phenoxymethyl]pyridine (83 mg, 0.28 mmol) as described in Example 7 part g), affording 5-[3-(pyridin-2-ylmethoxy)phenyl]-2-trifluoromethyl[1,8]naphthyridine (36 mg, 34%). δH (360 MHz, CDCl3) 5.28 (2H, s), 7.07-7.11 (2H, m), 7.20 (1H, dd, J 2.1 and 8.4), 7.23-7.30 (1H, m), 7.47-7.56 (3H, m), 7.73-7.78 (2H, m), 8.50 (1H, d, J 8.8), 8.61 (1H, d, J 4.6), 9.26 (1H, d, J 4.6). m/z (ES+) 382 [MH]+.

Sources & evidence

ORD record
ord-5f9b6500331c45a1a7b18fa56d6b5798
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

Loading…