Potassium Carbonate → 4-Chloro-5-[3-(tert-butyldimethylsiloxy)propoxy]-7-iodoisoindolinone

HRID 21316

반응식

HRID 21316 반응식
[Cl:1][C:2]1[C:10]([OH:11])=[CH:9][C:8]([I:12])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:13].C(=O)([O-])[O-].[K+].[K+].[C:20]([Si:24]([O:27][CH2:28][CH2:29][CH2:30]Br)([CH3:26])[CH3:25])([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[C:10]([O:11][CH2:30][CH2:29][CH2:28][O:27][Si:24]([C:20]([CH3:21])([CH3:23])[CH3:22])([CH3:25])[CH3:26])=[CH:9][C:8]([I:12])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:13]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 684892494-Chloro-5-hydroxy-7-iodoisoindolinone

생성물 1

HCID 684925174-Chloro-5-[3-(tert-butyldimethylsiloxy)propoxy]-7-iodoisoindolinone수율 79.7%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

실험 절차

In a similar manner to Step 1 of Example 429, 4-chloro-5-hydroxy-7-iodoisoindolinone (100 mg, 0.323 mmol) was dissolved in DMF (3.0 mL), and the solution was treated with potassium carbonate (134 mg, 0.969 mmol), tetrabutylammonium iodide (11.8 mg, 0.032 mmol) and tert-butyl(3-bromopropoxy)dimethylsilane (0.112 mL, 0.485 mmol), followed by purification by flash column chromatography (chloroform/methanol=99/1, 19/1) to obtain 4-chloro-5-[3-(tert-butyldimethylsiloxy)propoxy]-7-iodoisoindolinone (124 mg, yield 79%).

후처리

  1. customfollowed by purification by flash column chromatography (chloroform/methanol=99/1, 19/1)

출처 및 근거

ORD 기록
ord-466c88c3583141a7bc59d2c2395d2f4b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

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