Iodoethane → HCID 15435226, compound

HRID 1290099Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[C:21]3[C:20](=[O:22])[CH2:19][CH2:18][CH2:17][C:16]=3[NH:15][CH:14]=2)=[O:12])=[CH:6][CH:5]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:36][CH3:37]>CN(C)C=O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[C:21]3[C:20](=[O:22])[CH2:19][CH2:18][CH2:17][C:16]=3[N:15]([CH2:36][CH3:37])[CH:14]=2)=[O:12])=[CH:6][CH:5]=1)[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of N-(4-ethoxyphenyl)-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide (204 mg, 0.7 mmol), potassium carbonate (188 mg, 1.4 mmol), cesium carbonate (22 mg, 0.1 mmol), and iodoethane (0.08 mL, 1 mmol) in N,N-dimethylformamide was heated at 85° C. for 1 hour. The mixture was cooled and filtered using ethyl acetate. The solid was set aside; the organic layer was washed with water, dried over magnesium sulfate, filtered, concentrated in vacuo, and triturated with diethyl ether to give N-(4-ethoxyphenyl)-1-ethyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide (73 mg). The set-aside solid was slurried in aqueous hydrochloric acid, the precipitate collected, rinsed with water and dried to give additional amide (Compound 58) (94 mg). mp. 209°-210° C.

Workup

temperatureThe mixture was cooled
filtrationfiltered
washthe organic layer was washed with water
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customtriturated with diethyl ether

Sources & evidence

ORD record: ord-a37e9e240b5942279bd7fd4835cb8441
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05750702

Reaction notes

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