5-chloro-2-(trifluoromethyl)-1,8-Naphthyridine → 2'-Fluoro-5'-(7-trifluoromethyl[1,8]naphthyridin-4-yl)biphenyl-4-carbonitrile

HRID 1061789노트

반응식

HRID 1061789 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]=[CH:25][C:26]([F:37])=[C:27]([C:29]3[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][CH:30]=3)[CH:28]=2)OC1>>[F:37][C:26]1[CH:25]=[CH:24][C:23]([C:2]2[C:3]3[C:8](=[N:7][C:6]([C:12]([F:15])([F:14])[F:13])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)=[CH:28][C:27]=1[C:29]1[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][CH:30]=1

참가 물질

3

반응물 2

HCID 222852765-chloro-2-(trifluoromethyl)-1,8-NaphthyridineHCID 222853225'-(5,5-Dimethyl[1,3,2]dioxaborinan-2-yl)-2'-fluorobiphenyl-4-carbonitrile

생성물 1

HCID 102718752'-Fluoro-5'-(7-trifluoromethyl[1,8]naphthyridin-4-yl)biphenyl-4-carbonitrile수율 25%

실험 절차

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol) was coupled to 5′-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)-2′-fluorobiphenyl-4-carbonitrile (87 mg, 0.28 mmol) as described in Example 7 part g), affording 2′-fluoro-5′-(7-trifluoromethyl[1,8]naphthyridin-4-yl)biphenyl-4-carbonitrile (21 mg, 25%). δH (360 MHz, CDCl3) 7.41-7.46 (1H, m), 7.52-7.60 (3H, m), 7.71-7.82 (4H, m), 7.85 (1H, d, J 8.4), 8.52 (1H, d, J 8.8), 9.30 (1H, d, J 4.6). m/z (ES+) 394 [MH]+.

출처 및 근거

ORD 기록
ord-a434a87b0e734285bab53fedc74b05d7
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960598B2

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