Trifluoroacetic acid → 5,6-Dihydrophenanthridine

HRID 2181836ノート

反応式

HRID 2181836 の反応式
[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]

参加物

10

反応物 6

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

生成物 2

HCID 2199665,6-DihydrophenanthridineHCID 22482394HCID 22482394、化合物

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 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.;

後処理

  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)

出典と根拠

ORDレコード
ord-48ca3ab43e1a4464b8d6d3c21c51e4a1
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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