tert-Butyldimethylsilyl chloride → 7-Amino-4-(4-tert-butyldimethylsilyloxyphenyl)isoindolinone

HRID 21199Notes

Reaction equation

HRID 21199 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].C1CCN2C(=NCCC2)CC1>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:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[CH:14][CH:13]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 684918271h-Isoindol-1-one,7-amino-2,3-dihydro-4-(4-hydroxyphenyl)-

Product 1

HCID 684900227-Amino-4-(4-tert-butyldimethylsilyloxyphenyl)isoindolinoneYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 1 of Example 304, 7-amino-4-(4-hydroxyphenyl)isoindolinone (182 mg, 0.760 mmol) was dissolved in acetonitrile (9.1 mL), and the solution was treated with tert-butyldimethylsilyl chloride (206 mg, 1.37 mmol) and DBU (0.205 mL, 1.37 mmol), followed by purification by flash column chromatography (chloroform) to obtain 7-amino-4-(4-tert-butyldimethylsilyloxyphenyl)isoindolinone (182 mg, yield 68%).

Workup

  1. customfollowed by purification by flash column chromatography (chloroform)

Sources & evidence

ORD record
ord-24610f0b9d174d5ea4ca443ba6a1aa53
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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