Imidazole → 2-(3-Bromo-2-((tert-butyldimethylsilyl)oxy)propyl)isoindoline-1,3-dione

HRID 624579노트

반응식

HRID 624579 반응식
[Br:1][CH2:2][CH:3]([OH:16])[CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].N1C=CN=C1.[C:22]([Si:26](Cl)([CH3:28])[CH3:27])([CH3:25])([CH3:24])[CH3:23]>CN(C=O)C.CN(C1C=CN=CC=1)C.CCOC(C)=O>[Br:1][CH2:2][CH:3]([O:16][Si:26]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:28])[CH3:27])[CH2:4][N:5]1[C:6](=[O:15])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13]1=[O:14]

참가 물질

7

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2220382-(3-Bromo-2-hydroxypropyl)-1h-isoindole-1,3(2h)-dione

생성물 1

HCID 867229042-(3-Bromo-2-((tert-butyldimethylsilyl)oxy)propyl)isoindoline-1,3-dione

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

A solution of 2-(3-bromo-2-hydroxypropyl)isoindoline-1,3-dione (100 mg, 0.352 mmol) in DMF (0.5 mL) was added dropwise to a mixture of DMAP (43.0 mg, 0.352 mmol), imidazole (47.9 mg, 0.704 mmol) and tertbutyldimethylsilyl chloride (74.3 mg, 0.493 mmol) in DMF (1 mL). The mixture was stirred at room temperature for 18 hours. The mixture was diluted with EtOAc (20 ml) and washed with saturated NaHCO3(aq) (20 ml) and brine (3×10 ml). The organic phase was dried over magnesium sulfate and evaporated under vacuum. Purification by chromatography on silica, eluting with 0-100% EtOAc/hexane, afforded the title compound.

후처리

  1. washwashed with saturated NaHCO3(aq) (20 ml) and brine (3×10 ml)
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customevaporated under vacuum
  4. customPurification by chromatography on silica
  5. washeluting with 0-100% EtOAc/hexane

출처 및 근거

ORD 기록
ord-e45721bb52594e388b37666a6fc40acc
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303035B2

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