Trifluoroacetic acid → 5,6-Dihydrophenanthridine

HRID 2181855ノート

反応式

HRID 2181855 の反応式
[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]

参加物

10

反応物 6

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

生成物 2

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.;

後処理

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

出典と根拠

ORDレコード
ord-d2d6e18ff5384c21be8b2410b19f82de
出典データセット
uspto-grants-2005_05
特許番号
US06894061B2

反応ノート

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