Trifluoroacetic acid → 5,6-Dihydrophenanthridine

HRID 2181855노트

반응식

HRID 2181855 반응식
[F:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([CH3:16])[N:6]=[C:7]3[C:12]=2[CH:11]=[CH:10][CH:9]=[CH:8]3)[CH:3]=1.[BH4-].[Na+].FC(F)(F)C(O)=O.C1C=CC2C3C=CC=CC=3NCC=2C=1.C(N(CC)CC)C.[F:47][C:48]1[CH:49]=[C:50]([S:56](Cl)(=[O:58])=[O:57])[CH:51]=[CH:52][C:53]=1[O:54][CH3:55]>O1CCCC1.ClCCl>[CH:2]1[CH:15]=[CH:14][C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][CH2:5][C:4]=2[CH:3]=1.[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:6]([S:56]([C:50]1[CH:51]=[CH:52][C:53]([O:54][CH3:55])=[C:48]([F:47])[CH:49]=1)(=[O:57])=[O:58])[CH:5]2[CH3:16]

참가 물질

10

반응물 6

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 2199665,6-DihydrophenanthridineHCID 27745403-Fluoro-4-methoxybenzene-1-sulfonyl chlorideHCID 4311764Sodium borohydrideHCID 224823738-Fluoro-6-methylphenanthridine

생성물 2

HCID 2199665,6-DihydrophenanthridineHCID 224822898-Fluoro-5-[(3-fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

The intermediate dihydrophenanthridine was prepared from 8-fluoro-6-methylphenanthridine, (Example 32, Method A, Step b, 2.00 g, 9.45 mmol), by treatment with sodium borohydride (1.79 g, 47.4 mmol) and trifluoroacetic acid (2.9 mL, 37.9 mmol) in tetrahydrofuran (38 mL). In a separate, second step, the dihydrophenanthridine was treated with triethylamine (2.7 mL, 19 mmol) and 3-fluoro-4-methoxybenzenesulfonyl chloride (0.78 g, 3.5 mmol, 1.1 equivalents) in dichloromethane (5 mL) according to the procedure and in the same manner as described in Example 32, Method A, Step d. The crude product was purified by re-crystallization from a mixture of ethyl acetate-hexane to yield 8-fluoro-5-[(3-fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine as a homogeneous solid (1.08 g, 84% from the dihydrophenanthridine), m.p. 146-147° C.;

후처리

  1. customThe crude product was purified by re-crystallization from a mixture of ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-d2d6e18ff5384c21be8b2410b19f82de
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06894061B2

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