Triethylamine → 4-Chloro-7-(benzofuran-2-yl)isoindolinone

HRID 21113

Reaction equation

HRID 21113 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8](I)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12].[O:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH:15]=[C:14]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>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:14]2[O:13][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH:15]=2)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 2776266Benzo[b]furan-2-boronic acidHCID 684927354-Chloro-7-iodoisoindolinone

Product 1

HCID 684925464-Chloro-7-(benzofuran-2-yl)isoindolinoneYield 18.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 2 of Example 1, 4-chloro-7-iodoisoindolinone (80.0 mg, 0.273 mmol) was dissolved in acetonitrile (4.0 mL), and the solution was treated with 2-benzofuraneboronic acid (133 mg, 0.819 mmol), palladium acetate (7.4 mg, 0.033 mmol), tri(o-tolyl)phosphine (20 mg, 0.066 mmol) and triethylamine (0.381 mL, 2.73 mmol), followed by purification by preparative thin-layer chromatography (chloroform/acetonitrile=15/1) to obtain Compound 170 (14.3 mg, yield 18%).

Workup

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

Sources & evidence

ORD record
ord-731c89dbdef6467ca5f1aba701c7dcf9
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

Loading…