Trifluoroacetic acid → 5,6-Dihydrophenanthridine

HRID 2181844ノート

反応式

HRID 2181844 の反応式
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]3[C:10](=[C:11]([CH2:16][CH3:17])[N:12]=2)[CH:9]=[C:8]([F:18])[CH:7]=[CH:6]3)[CH:3]=1.[BH4-].[Na+].FC(F)(F)C(O)=O.C1C=CC2C3C=CC=CC=3NCC=2C=1.C(N(CC)CC)C.[CH3:49][O:50][C:51]1[CH:56]=[CH:55][C:54]([S:57](Cl)(=[O:59])=[O:58])=[CH:53][CH:52]=1>O1CCCC1.ClCCl>[CH:8]1[CH:7]=[CH:6][C:5]2[C:4]3[CH:3]=[CH:2][CH:15]=[CH:14][C:13]=3[NH:12][CH2:11][C:10]=2[CH:9]=1.[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[N:12]([S:57]([C:54]3[CH:53]=[CH:52][C:51]([O:50][CH3:49])=[CH:56][CH:55]=3)(=[O:59])=[O:58])[CH:11]([CH2:16][CH3:17])[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([F:18])[CH:9]=3)[C:4]=2[CH:3]=1

参加物

10

反応物 6

HCID 6422Trifluoroacetic acidHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 2199665,6-DihydrophenanthridineHCID 4311764Sodium borohydrideHCID 224823802-Bromo-6-ethyl-8-fluorophenanthridine

生成物 2

HCID 2199665,6-DihydrophenanthridineHCID 224823412-Bromo-6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-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 2-bromo-6-ethyl-8-fluorophenanthridine (3.27 g, 10.8 mmol) by treatment with sodium borohydride (2.03 g, 53.8 mmol) and trifluoroacetic acid (3.31 mL, 43.0 mmol) in tetrahydrofuran (43 mL). In a separate, second step, the dihydrophenanthridine was treated with triethylamine (9.0 mL, 65 mmol) and 4-methoxybenzenesulfonyl chloride (2.44 g, 11.8 mmol) in dichloromethane (11 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 afford 2-bromo-6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine as a homogeneous, yellow, crystalline, solid, m.p. 133-136° 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 (1:9 to 1:4 gradient)

出典と根拠

ORDレコード
ord-931871b17bf045cf984988a113911d7b
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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