Trifluoroacetic acid → 5,6-Dihydrophenanthridine

HRID 2181848노트

반응식

HRID 2181848 반응식
[CH2:1]([C:3]1[N:4]=[C:5]2[C:10](=[C:11]3[C:16]=1[CH:15]=[C:14]([F:17])[CH:13]=[CH:12]3)[CH:9]=[CH:8][CH:7]=[CH:6]2)[CH3:2].[BH4-].[Na+].FC(F)(F)C(O)=O.C1C=CC2C3C=CC=CC=3NCC=2C=1.C(N(CC)CC)C.[Cl:48][C:49]1[CH:50]=[C:51]([S:57](Cl)(=[O:59])=[O:58])[CH:52]=[CH:53][C:54]=1[O:55][CH3:56]>O1CCCC1.ClCCl>[CH:14]1[CH:13]=[CH:12][C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[NH:4][CH2:3][C:16]=2[CH:15]=1.[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]1[S:57]([C:51]1[CH:52]=[CH:53][C:54]([O:55][CH3:56])=[C:49]([Cl:48])[CH:50]=1)(=[O:58])=[O:59])[CH3:2]

참가 물질

10

반응물 6

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 2199665,6-DihydrophenanthridineHCID 4311764Sodium borohydrideHCID 167674273-Chloro-4-methoxybenzene-1-sulfonyl chlorideHCID 22482260HCID 22482260, 화합물

생성물 2

HCID 2199665,6-DihydrophenanthridineHCID 22482342HCID 22482342, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

The intermediate dihydrophenanthridine was prepared from 6-ethyl-8-fluorophenanthridine, (Example 40, Step b, 0.40 g, 1.8 mmol), by treatment with sodium borohydride (0.40 g, 10.6 mmol) and trifluoroacetic acid (0.55 mL, 7.1 mmol) in tetrahydrofuran (7 mL). In a separate, second step, the dihydrophenanthridine was treated with triethylamine (0.9 mL, 6.4 mmol) and 3-chloro-4-methoxybenzenesulfonyl chloride (0.51 g, 2.1 mmol, 2.1 equivalents) in dichloromethane (5 mL), according to the procedure and in the same manner as described in Example 32, Method A, Step d, to afford 6-ethyl-8-fluoro-5-[(3-chloro-4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine as a crude product, which was utilized without further purification.

출처 및 근거

ORD 기록
ord-1afc60d4b4184dada63199b24b44fd26
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06894061B2

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