Dimethylformamide → HCID 57608231, compound

HRID 1171229Notes

Reaction equation

CN(C)C=O.[OH:6][C:7]1[CH:8]=[CH:9][C:10]2[CH:14]=[C:13]([CH2:15][N:16]3[C:24](=[O:25])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]3=[O:26])[S:12][C:11]=2[CH:27]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O.C(OCC)(=O)C>[CH2:34]([O:6][C:7]1[CH:8]=[CH:9][C:10]2[CH:14]=[C:13]([CH2:15][N:16]3[C:17](=[O:26])[C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:24]3=[O:25])[S:12][C:11]=2[CH:27]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To an N,N-dimethylformamide (3 mL) solution of 2-(6-hydroxy-benzo[b]thiophen-2-ylmethyl)-isoindole-1,3-dione (121 mg, 0.391 mmol) were added potassium carbonate (162 mg, 1.17 mmol) and benzyl bromide (70 μL, 0.587 mmol). The mixture was stirred at 100° C. for 30 minutes. The reaction mixture was distributed between ethyl acetate and water. The organic layer was washed with water followed by drying over anhydrous magnesium sulfate and filtering. The filtrate was concentrated under a reduced pressure and the resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1 to 4:1 and then 1:1) to obtain the title compound (144 mg, 92%).

Workup

washThe organic layer was washed with water
dry with materialby drying over anhydrous magnesium sulfate
filtrationfiltering
concentrationThe filtrate was concentrated under a reduced pressure
customthe resulting residue was purified by silica gel chromatography (hexane

Sources & evidence

ORD record: ord-82eaf7dc63ae492297b01b336fddc886
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829585B2

Reaction notes

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