5-chloro-2-(trifluoromethyl)-1,8-Naphthyridine → HCID 10222033, compound

HRID 1061808Notes

Reaction equation

HRID 1061808 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]=[CH:25][C:26]([F:36])=[C:27]([CH:35]=2)[CH2:28][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)OC1>>[F:36][C:26]1[CH:25]=[CH:24][C:23]([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:35][C:27]=1[CH2:28][N:29]1[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1

Participants

3

Reactant 2

HCID 222852765-chloro-2-(trifluoromethyl)-1,8-NaphthyridineHCID 222853134-[[5-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)-2-fluorophenyl]methyl]morpholine

Product 1

HCID 10222033HCID 10222033, compoundYield 12%

Procedure

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol) was coupled to 4-[5-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)-2-fluorobenzyl]morpholine (86 mg, 0.28 mmol) as described in Example 7 part g), affording 5-(4-fluoro-3-morpholin-4-ylmethylphenyl)-2-trifluoromethyl[1,8]naphthyridine (10 mg, 12%). δH (360 MHz, CDCl3) 2.54 (4H, t, J 4.2), 3.68 (2H, s), 3.71 (4H, t, J 4.4), 7.26 (1H, t, 8.8), 7.37 (1H, m), 7.55-7.58 (2H, m), 7.82 (1H, d, J 8.4), 8.49 (1H, d, J 8.4), 9.27 (1H, d, J 4.2). m/z (ES+) 392 [MH]+.

Sources & evidence

ORD record
ord-46c3d71350174428b71452644c453f38
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

Loading…