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

HRID 624579Notes

Reaction equation

HRID 624579 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e45721bb52594e388b37666a6fc40acc
Source dataset
uspto-grants-2016_04
Patent number
US09303035B2

Reaction notes

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