Water → 1h-Isoindol-1-one,7-amino-2,3-dihydro-4-(4-hydroxyphenyl)-

HRID 21198Notes

Reaction equation

HRID 21198 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5](Br)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2.[C:13](=[O:16])([O-])[O-].[K+].[K+].O>C(COC)OC>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:2]2[CH:3]=[CH:4][C:13]([OH:16])=[CH:9][CH:10]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 197019327-Amino-4-bromo-2,3-dihydroisoindol-1-one

Product 1

HCID 684918271h-Isoindol-1-one,7-amino-2,3-dihydro-4-(4-hydroxyphenyl)-Yield 181.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

In a similar manner to Step 1 of Example 152, 7-amino-4-bromoisoindolinone (200 mg, 0.880 mmol) was dissolved in dimethoxyethane (14 mL); and the solution was treated with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenol (387 mg, 1.76 mmol), [bis(diphenylphosphino)ferrocene]dichloropalladium (57.4 mg, 0.0704 mmol), potassium carbonate (607 mg, 4.40 mmol) and water (0.32 mL), followed by purification by slurry using chloroform to obtain 7-amino-4-(4-hydroxyphenyl)isoindolinone (192 mg, yield 91%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-b24b3e5868fe4fc6b86b9220500a2140
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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