Trifluoroacetic acid → 5,6-Dihydrophenanthridine

HRID 2181848ノート

反応式

HRID 2181848 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.[Cl:48][C:49]1[CH:50]=[C:51]([S:57](Cl)(=[O:59])=[O:58])[CH:52]=[CH:53][C:54]=1[O:55][CH3:56]>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:57]([C:51]1[CH:52]=[CH:53][C:54]([O:55][CH3:56])=[C:49]([Cl:48])[CH:50]=1)(=[O:58])=[O:59])[CH3:2]

参加物

10

反応物 6

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 2199665,6-DihydrophenanthridineHCID 4311764Sodium borohydrideHCID 167674273-Chloro-4-methoxybenzene-1-sulfonyl chlorideHCID 22482260HCID 22482260、化合物

生成物 2

HCID 2199665,6-DihydrophenanthridineHCID 22482342HCID 22482342、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-fluorophenanthridine, (Example 40, Step b, 0.40 g, 1.8 mmol), by treatment with sodium borohydride (0.40 g, 10.6 mmol) and trifluoroacetic acid (0.55 mL, 7.1 mmol) in tetrahydrofuran (7 mL). In a separate, second step, the dihydrophenanthridine was treated with triethylamine (0.9 mL, 6.4 mmol) and 3-chloro-4-methoxybenzenesulfonyl chloride (0.51 g, 2.1 mmol, 2.1 equivalents) in dichloromethane (5 mL), according to the procedure and in the same manner as described in Example 32, Method A, Step d, to afford 6-ethyl-8-fluoro-5-[(3-chloro-4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine as a crude product, which was utilized without further purification.

出典と根拠

ORDレコード
ord-1afc60d4b4184dada63199b24b44fd26
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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