Trifluoroacetic acid → 5,6-Dihydrophenanthridine

HRID 2181836노트

반응식

HRID 2181836 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.[CH3:48][O:49][C:50]1[CH:55]=[CH:54][C:53]([S:56](Cl)(=[O:58])=[O:57])=[CH:52][C:51]=1[CH3:60]>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:56]([C:53]1[CH:54]=[CH:55][C:50]([O:49][CH3:48])=[C:51]([CH3:60])[CH:52]=1)(=[O:58])=[O:57])[CH3:2]

참가 물질

10

반응물 6

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 2199665,6-DihydrophenanthridineHCID 4311764Sodium borohydrideHCID 159153174-Methoxy-3-methylbenzene-1-sulfonyl chlorideHCID 22482260HCID 22482260, 화합물

생성물 2

HCID 2199665,6-DihydrophenanthridineHCID 22482394HCID 22482394, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

The intermediate dihydrophenanthridine was prepared from 6-ethyl-8-fluoro-phenanthridine, (Example 40, Step b, 0.79 g, 3.48 mmol), by treatment with sodium borohydride (0.79 g, 21 mmol) and trifluoroacetic acid (1.1 mL, 14 mmol) in tetrahydrofuran (18 mL). In a separate, second step, the dihydrophenanthridine was treated with triethylamine (0.8 mL, 6 mmol) and 4-methoxy-3-methylbenzenesulfonyl chloride (0.66 g, 3.0 mmol, 2 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 flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:19 to 3:7 gradient), to yield 6-ethyl-8-fluoro-5-[(4-methoxy-3-methylphenyl)sulfonyl]-5,6-dihydrophenanthridine as a homogeneous, white solid (0.57 g, 92% from the dihydrophenanthridine), m.p. 140° C.;

후처리

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (1:19 to 3:7 gradient)

출처 및 근거

ORD 기록
ord-48ca3ab43e1a4464b8d6d3c21c51e4a1
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06894061B2

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