5-chloro-2-(trifluoromethyl)-1,8-Naphthyridine → HCID 10160833, compound

HRID 1061792Notes

Reaction equation

HRID 1061792 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[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[S:38]([CH3:41])(=[O:40])=[O:39]>>[F:16][C:17]1[C:18]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[S:38]([CH3:41])(=[O:40])=[O:39])=[CH:19][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:21][CH:22]=1

Participants

3

Reactant 2

HCID 222852765-chloro-2-(trifluoromethyl)-1,8-NaphthyridineHCID 222853232-(2-Fluoro-2'-(methanesulfonyl)biphenyl-5-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Product 1

HCID 10160833HCID 10160833, compoundYield 33%

Procedure

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol) was coupled to 2-(2-fluoro-2′-(methanesulfonyl)biphenyl-5-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (105 mg, 0.28 mmol) as described in Example 7 part g), affording 5-(6-fluoro-2′-methanesulfonylbiphenyl-3-yl)-2-trifluoromethyl[1,8]-naphthyridine (32 mg, 33%). δH (360 MHz, CDCl3) 2.97 (3H, s), 7.38-7.46 (2H, m), 7.54-7.74 (5H, m), 7.87 (1H, d, J 8.4), 8.26 (1H, dd, J 1.2 and 7.9), 8.79 (1H, d, J 8.4), 9.27 (1H, d, J 4.2). m/z (ES+) 447 [MH]+.

Sources & evidence

ORD record
ord-d1b95f4a5a374edf9148e2cb0a6ace3c
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

Loading…