Triethylamine → 5-[(Z)-(5-bromo-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-N-[2-(diethylamino)ethyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide

HRID 1243901Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.N1([C:17]([C:19]2[C:20]([CH3:27])=[C:21]([CH:25]=O)[NH:22][C:23]=2[CH3:24])=[O:18])C=CN=C1.[CH2:28]([N:30]([CH2:34][CH3:35])[CH2:31][CH2:32][NH2:33])[CH3:29].C(N(CC)CC)C>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:25]\[C:21]1[NH:22][C:23]([CH3:24])=[C:19]([C:17]([NH:33][CH2:32][CH2:31][N:30]([CH2:34][CH3:35])[CH2:28][CH3:29])=[O:18])[C:20]=1[CH3:27]

Participants

Conditions

Temperature: 62.5 °C

Procedure

A 0.1 L flask fitted with a thermometer, condenser, beating mantle, nitrogen inlet and magnetic stirring was charged with, 3.0 g 5-Bromooxindole, 3.03 g 4-(1H-imidazol-1-ylcarbonyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde, 3.24 g N,N-Diethylethylene diamine, 4.23 g Triethylamine and 30 ml Tetrahydrofuran. The mixture was heated to 60-65° C. for 8 hours, then cooled to ambient temperature. 10 ml Tetrahydrofuran was added to aid stirring and the reaction mixture was filtered. Drying provided 3.7 g (57.7%) first crop of 5-[(Z)-(5-bromo-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-N-[2-(diethylamino)ethyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide. The mother liquors are cooled to −10° C. for 6 h for an additional 1.9 g (29.6%). 1HNMR (DMSO): δ 8.08 (1H, s); 7.75 (1H, s); 7.41 (1H, s); 7.24 (1H, d); 6.81 (1H, d); 3.31 (4H, bs); 2.46 (14H, bm); 0.96 (6H, t).

Workup

customA 0.1 L flask fitted with a thermometer, condenser
temperaturecooled to ambient temperature
stirringstirring
filtrationthe reaction mixture was filtered
customDrying

Sources & evidence

ORD record: ord-7a32ff25457f488f8f0f3ce0c66abe2b
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119209B2

Reaction notes

Loading…