4-(Hydroxymethyl)benzeneboronic acid → 3-Amino-4-(hydroxymethylphenyl)-6-bromophthalimide

HRID 20999

Reaction equation

HRID 20999 reaction equation
[NH2:1][C:2]1[C:12](I)=[CH:11][C:10]([Br:14])=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6].[OH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.S1C=CC=C1C([O-])=O.[Cu+]>[NH2:1][C:2]1[C:12]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH2:16][OH:15])=[CH:11][C:10]([Br:14])=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6].[NH2:1][C:2]1[C:12]([C:20]2[CH:21]=[CH:22][C:17]([CH2:16][OH:15])=[CH:18][CH:19]=2)=[CH:11][C:10]([C:12]2[CH:11]=[CH:10][C:4]([CH2:5][OH:6])=[CH:3][CH:2]=2)=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6]

Participants

7

Reactant 2

HCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 684887173-Amino-4-iodo-6-bromophthalimide

Product 2

HCID 684912043-Amino-4-(hydroxymethylphenyl)-6-bromophthalimideYield 64%HCID 684929023-Amino-4,6-di(4-hydroxymethylphenyl)phthalimideYield 29%

Reagents, catalysts & solvents 3

HCID 11194830Cuprous 2-thiophenecarboxylateCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 2 of Example 2, 3-amino-4-iodo-6-bromophthalimide (100 mg, 0.273 mmol) was dissolved in THF (7 mL), and the solution was treated with 4-hydroxymethylphenylboronic acid (83 mg, 0.55 mmol), tetrakis(triphenylphosphine)palladium (25 mg, 0.022 mmol) and copper(I)thiophene-2-carboxylate (104 mg, 0.546 mmol), followed by purification by preparative thin-layer chromatography (chloroform/methanol=15/1) to obtain 3-amino-4-(hydroxymethylphenyl)-6-bromophthalimide (61 mg, yield 64%) and 3-amino-4,6-di(4-hydroxymethylphenyl)phthalimide (29 mg, yield 29%).

Workup

  1. customfollowed by purification by preparative thin-layer chromatography (chloroform/methanol=15/1)

Sources & evidence

ORD record
ord-72bdee8320374be6a672ca3798ce76e8
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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