Water → HCID 58763422, compound

HRID 858282Notes

Reaction equation

[C:1]([S:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[C:16]([O:18][CH3:19])=[O:17])(=[O:3])[CH3:2].[H-].[Na+].Br[CH2:23][C:24]1[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=1)[C:27]([O:29][CH3:30])=[O:28].O>CN(C=O)C.CCOC(C)=O>[C:1]([S:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:23][C:24]2[CH:33]=[CH:32][CH:31]=[C:26]([C:27]([O:29][CH3:30])=[O:28])[CH:25]=2)[C:8]=1[C:16]([O:18][CH3:19])=[O:17])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of methyl 3-[2-(acetylthio)ethyl]-1H-indole-2-carboxylate (0.300 g, 1.1 mmol) in DMF (5 mL) was added sodium hydride (60% dispersion in mineral oil, 0.048 g, 1.2 mmol) at −10° C., and the mixture was stirred at −10° C. for 15 minutes. To the mixture was added methyl 3-(bromomethyl)-benzoate (0.273 g, 1.2 mmol) at −15° C., and the reaction mixture was allowed to gradually come to room temperature and stirred overnight. To the mixture were added H2O (20 mL) and EtOAc (20 mL). The organic layer was dried over Na2SO4 and concentrated to give methyl 3-[2-(acetylthio)ethyl]-1-[[3-(methoxycarbonyl)phenyl]-methyl]-1H-indole-2-carboxylate as an oil (0.430 g). This material was used for the next reaction without further purification: 1H NMR (DMSO-d6) 2.32 (s, 3H), 3.10 (t, J=6.52 Hz, 2H), 3.31 (t, J=6.52 Hz, 2H), 3.80 (s, 3H), 3.83 (s, 3H), 5.85 (s, 2H), 7.17–7.23 (m, 2H), 7.34 (t, J=7.7 Hz, 1H), 7.42 (t, J=7.6 Hz, 1H), 7.56 (d, J=8.5 Hz, 1H), 7.66 (s, 1H), 7.80 (d, J=7.8 Hz, 1H), 7.83 (d, J=8.1 Hz, 1H).

Workup

customto gradually come to room temperature
stirringstirred overnight
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-0242997f85af44e2b6961cab99fde368
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148250B2

Reaction notes

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