Triethylamine → 3-Amino-6-(benzofuran-2-yl)phtalimide

HRID 21114

Reaction equation

HRID 21114 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:10](Br)=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6].[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH:16]=[C:15]1B(O)O.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([C:15]2[O:14][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH:16]=2)=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 2776266Benzo[b]furan-2-boronic acidHCID 684890894-amino-7-bromo-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

HCID 684922653-Amino-6-(benzofuran-2-yl)phtalimideYield 33%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 2 of Example 1, 3-amino-6-bromophthalimide (80.0 mg, 0.332 mmol) was dissolved in acetonitrile (4.0 mL), and, the solution was treated with 2-benzofuraneboronic acid (161 mg, 0.996 mmol), palladium acetate (9.0 mg, 0.040 mmol), tri(o-tolyl)phosphine (24.3 mg, 0.080 mmol) and triethylamine (0.463 mL, 3.32 mmol), followed by purification by preparative thin-layer chromatography (chloroform/acetonitrile=15/1) to obtain Compound 171 (30.1 mg, yield 33%).

Workup

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

Sources & evidence

ORD record
ord-a4efae9c91d74fb0a4807b3ad512d487
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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