Tetrabutylammonium Fluoride → Bpr-0L075

HRID 710324노트

반응식

HRID 710324 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 10359957Bpr-0L075수율 108.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6433c02f67ba429f87cf496d8a538c65
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181182B2

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