3-[3-(5,5-Dimethyl[1,3,2]dioxaborinan-2-yl)-5-fluorophenyl]pyridine → 5-(3-Fluoro-5-pyridin-3-ylphenyl)-2-trifluoromethyl[1,8]naphthyridine

HRID 1061797노트

반응식

HRID 1061797 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.CC1(C)COB([C:23]2[CH:24]=[C:25]([C:30]3[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=3)[CH:26]=[C:27]([F:29])[CH:28]=2)OC1>>[F:29][C:27]1[CH:28]=[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:24]=[C:25]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH:26]=1

참가 물질

3

반응물 2

HCID 222852723-[3-(5,5-Dimethyl[1,3,2]dioxaborinan-2-yl)-5-fluorophenyl]pyridineHCID 222852765-chloro-2-(trifluoromethyl)-1,8-Naphthyridine

생성물 1

HCID 102925055-(3-Fluoro-5-pyridin-3-ylphenyl)-2-trifluoromethyl[1,8]naphthyridine수율 24%

실험 절차

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol) was coupled to 3-[3-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)-5-fluorophenyl]pyridine (80 mg, 0.28 mmol) as described in Example 7 part g), affording 5-(3-fluoro-5-pyridin-3-ylphenyl)-2-trifluoromethyl[1,8]naphthyridine (19 mg, 24%). δH (360 MHz, CDCl3) 7.24-7.63 (1H, m), 7.41-7.45 (1H, m), 7.48-7.52 (2H, m), 7.63 (1H, d, J 4.6), 7.86 (1H, d, J 8.8), 7.92 (1H, dt, J 8.1 and 1.9), 8.55 (1H, d, J 8.8), 8.69 (1H, dd, J 1.6 and 4.7), 8.90 (1H, d, J 1.8), 9.32 (1H, d, J 4.6). m/z (ES+) 370 [MH]+.

출처 및 근거

ORD 기록
ord-3a0b8c17172c4509953e42b752e51408
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960598B2

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