5-chloro-2-(trifluoromethyl)-1,8-Naphthyridine → 5-(4-Fluoro-3-methoxyphenyl)-2-trifluoromethyl[1,8]naphthyridine

HRID 1061820

반응식

HRID 1061820 반응식
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[O:32][CH3:33]>>[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[O:32][CH3:33]

참가 물질

3

반응물 2

HCID 222852765-chloro-2-(trifluoromethyl)-1,8-NaphthyridineHCID 222853052-(4-Fluoro-3-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 99450085-(4-Fluoro-3-methoxyphenyl)-2-trifluoromethyl[1,8]naphthyridine수율 83%

실험 절차

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (923 mg, 4.0 mmol) was coupled to 2-(4-fluoro-3-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (1.30 g, 5.2 mmol) as described in Example 3 part g), affording 5-(4-fluoro-3-methoxyphenyl)-2-trifluoromethyl[1,8]naphthyridine (1.06 g, 83%). δH (360 MHz, CDCl3) 3.95 (3H, s), 6.99-7.04 (1H, m), 7.06 (1H, dd, J 7.7 and 2.1), 7.30 (1H, dd, J 2.5 and 8.4), 7.56 (1H, d, J 4.2), 7.82 (1H, d, J 8.4), 8.52 (1H, d, J 8.4), 9.27 (1H, d, J 4.2). m/z (ES+) 323 [MH]+.

출처 및 근거

ORD 기록
ord-1a882e93ca4545bc900ff85dfc2f0027
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960598B2

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