Water → HCID 68490965, compound

HRID 21196Notes

Reaction equation

HRID 21196 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].N12CCCN=C1CCCCC2.O>C(#N)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:17]=[CH:16][C:15]([O:18][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])=[C:14]([O:19][CH3:20])[CH:13]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 28928tert-Butyldimethylsilyl chloride2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 684876617-Amino-4-(4-hydroxy-3-methoxyphenyl)isoindolinone

Product 1

HCID 68490965HCID 68490965, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7-Amino-4-(4-hydroxy-3-methoxyphenyl)isoindolinone (50.0 mg, 0.185 mmol) was dissolved in acetonitrile (2.5 mL), and the solution was added with tert-butyldimethylsilyl chloride (33.5 mg, 0.222 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.033 mL, 0.22 mmol), followed by stirring at room temperature for 1.3 hours. The mixture was added with tert-butyldimethylsilyl chloride (33.5 mg, 0.222 mmol) and DBU (0.033 mL, 0.22 mmol), followed by further stirring for 1 hour. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by preparative thin-layer chromatography (chloroform/acetonitrile=2/1) to obtain 7-amino-4-(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)isoindolinone (51.1 mg, yield 72%).

Workup

  1. stirringby further stirring for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by preparative thin-layer chromatography (chloroform/acetonitrile=2/1)

Sources & evidence

ORD record
ord-78c5d8d1945d4cd0a61a9be59df50545
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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