3-(2-Bromoethyl)indole → HCID 58031709, compound

HRID 560703Notes

Reaction equation

HRID 560703 reaction equation
FC(F)(F)C1C=CC(CBr)=CC=1.Br[CH2:14][CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][CH:17]=1.[CH3:25][C:26]1[N:27]=[C:28]([N:36]2[CH2:40][CH2:39][NH:38][C:37]2=[O:41])[S:29][C:30]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32]>>[NH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([CH2:15][CH2:14][N:38]2[CH2:39][CH2:40][N:36]([C:28]3[S:29][C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:26]([CH3:25])[N:27]=3)[C:37]2=[O:41])=[CH:17]1

Participants

4

Reactant 3

HCID 769243-(2-Bromoethyl)indoleHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 57919776Ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 58031709HCID 58031709, compoundYield 40%

Procedure

Following the procedure as described in Example 13, making variations as required to replace 4-(trifluoromethyl)benzyl bromide with 3-(2-bromoethyl)-1H-indole to react with ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained as a colorless solid in 40% yield: 1H NMR (300 MHz, CDC3) δ 8.09 (s, 1H), 7.63 (d, J=7.8 Hz, 1H), 7.39-7.36 (m, 1H), 7.24-7.09 (m, 3H), 4.29 (q, J=7.1 Hz, 2H), 4.04-3.99 (m, 2H), 3.69 (t, J=7.2 Hz, 2H), 3.52-3.46 (m, 2H), 3.08 (t, J=7.1 Hz, 2H), 2.62 (s, 3H), 1.34 (t, J=7.1 Hz, 3H); MS (ES+) m/z 399.3 (M+1).

Sources & evidence

ORD record
ord-a7efd91b38f74a39be1804af28f5d66f
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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