Tetrabutylammonium Fluoride → Bpr-0L075

HRID 710324ノート

反応式

HRID 710324 の反応式
[Si]([C:8]1[N:9](C(=O)C)[C:10]2[C:15]([C:16]=1[C:17](=[O:30])[C:18]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=1)=[CH:14][CH:13]=[C:12]([O:31][CH3:32])[CH:11]=2)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:32][O:31][C:12]1[CH:11]=[C:10]2[C:15]([C:16]([C:17]([C:18]3[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=3)=[O:30])=[CH:8][NH:9]2)=[CH:14][CH:13]=1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 667265851-(2-(tert-Butyldimethylsilyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-indol-1-yl)ethanone

生成物 1

HCID 10359957Bpr-0L075収率 108.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A mixture of the product of Step A (0.52 g, 1.05 mmol) and 1M TBAF in THF (1 ml) in THF (10 ml) was refluxed for 2 h. The solvent was evaporated and the residue was taken in EtOAc, washed with 1M HCl and organic layer was passed through silica gel bead. The solvent was evaporated and the residue was crystallized from MeOH to give the desired product (0.39 g; 100%), as creamy solid. 1H-NMR (CDCl3) 3.83 (s, 3H); 3.87 (s, 3H); 3.91 (s, 3H); 6.93-6.96 (m, 2H); 7.06 (s, 2H); 7.62 (s, 1H); 8.22 (d, 1H, J=9.36 Hz); 9.24 (broad s, 1H).

後処理

  1. temperaturewas refluxed for 2 h
  2. customThe solvent was evaporated
  3. washwashed with 1M HCl and organic layer
  4. customThe solvent was evaporated
  5. customthe residue was crystallized from MeOH

出典と根拠

ORDレコード
ord-6433c02f67ba429f87cf496d8a538c65
出典データセット
uspto-grants-2015_11
特許番号
US09181182B2

反応ノート

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