Trifluoroacetic acid → 5,6-Dihydrophenanthridine

HRID 2181831노트

반응식

HRID 2181831 반응식
[CH3:1][O:2][C:3]1[C:4]2[C:13]([CH:14]=[CH:15][CH:16]=1)=[C:12]1[C:7]([CH:8]=[CH:9][CH:10]=[CH:11]1)=[N:6][C:5]=2[CH3:17].[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][CH:51]=1>O1CCCC1.ClCCl>[CH:16]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.[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[CH:5]([CH3:17])[N:6]([S:56]([C:53]1[CH:52]=[CH:51][C:50]([O:49][CH3:48])=[CH:55][CH:54]=1)(=[O:58])=[O:57])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=12

참가 물질

10

반응물 6

HCID 6422Trifluoroacetic acidHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 2199665,6-DihydrophenanthridineHCID 4311764Sodium borohydrideHCID 224822867-Methoxy-6-methylphenanthridine

생성물 2

HCID 2199665,6-DihydrophenanthridineHCID 224823397-Methoxy-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

The intermediate dihydrophenanthridine was prepared from 7-methoxy-6-methylphenanthridine, (Example 36, Step b, 0.61 g, 2.7 mmol), by treatement with sodium borohydride (0.62 g, 16 mmol) and trifluoroacetic acid (0.84 mL, 10.8 mmol) in tetrahydrofuran (12 mL). In a separate, second step, the dihydrophenanthridine was treated with triethylamine (0.77 mL, 5.5 mmol) and 4-methoxybenzenesulfonyl chloride (0.57 g, 2.8 mmol, 2 equivalents) in dichloromethane (3 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 (1:9 to 1:4 gradient), to yield 7-methoxy-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine as a white solid (0.17 g, 33% from the dihydrophenanthridine);

후처리

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (1:9 to 1:4 gradient)

출처 및 근거

ORD 기록
ord-1e307605e93a432c9d2ae43a1ed37840
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06894061B2

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