Dimethylformamide → 2-{2-[3-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-1-yl]ethyl}-1H-isoindole-1,3(2H)-dione

HRID 731560Notes

Reaction equation

Cl[CH2:2][CH2:3][N:4]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[C:6]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[CH:5]1.[C:22]([O-:33])(=O)[C:23]1[C:24](=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:25]([O-])=[O:26].[K+].[K+].C[N:37](C=O)C>O>[C:16]1([S:13]([C:6]2[C:7]3[C:8](=[N:9][CH:10]=[CH:11][CH:12]=3)[N:4]([CH2:3][CH2:2][N:37]3[C:25](=[O:26])[C:24]4[C:23](=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:22]3=[O:33])[CH:5]=2)(=[O:15])=[O:14])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 115 °C

Procedure

A solution of 1-(2-chloroethyl)-3-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (3.84 g, 12.0 mmol) in DMF is treated with potassium phthalate (2.78 g, 15.0 mmol, heated at 115° C. for 16 h, cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The resultant residue is crystallized from CH2Cl2/hexane to afford the title compound as a white solid, 4.54 g, characterized by HNMR analysis.

Workup

temperaturecooled to room temperature
extractionextracted with ethyl acetate
washThe combined extracts are washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe resultant residue is crystallized from CH2Cl2/hexane

Sources & evidence

ORD record: ord-bb83758a7b0a4e3d966adc050babc6c2
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585873B2

Reaction notes

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