Cesium carbonate → tert-butyl 2-(1-benzyl-2-ethyl-1H-indol-4-yloxy)acetate

HRID 397858Notes

Reaction equation

[CH2:1]([C:3]1[N:4]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]2[C:10]([CH:11]=1)=[C:9]([OH:12])[CH:8]=[CH:7][CH:6]=2)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>CN(C=O)C.O>[C:31]([O:30][C:28](=[O:29])[CH2:27][O:12][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[C:3]([CH2:1][CH3:2])[N:4]2[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:34])([CH3:33])[CH3:32]

Participants

Conditions

Temperature: 35 °C

Procedure

2-Ethyl-4-hydroxy-1-(phenylmethyl)-1H-indole (5.82 g, 20 mmol) is added to 7.82 g (24 mmol) cesium carbonate in 25 mL DMF and the mixture is stirred at 35° C. for 30 minutes. After cooling to 20° C., a solution of tert-butyl bromoacetate (4.65 g, 23.8 mmol) in 5 mL DMF is added and stirring maintained until the reaction is judged complete by TLC analysis (several hours). The mixture is diluted with water and extracted with ethyl acetate. The ethyl acetate solution is washed with brine, dried (MgSO4) and concentrated at reduced pressure to give 6.8 g of solid.

Workup

temperatureAfter cooling to 20° C.
stirringstirring
temperaturemaintained until the reaction
customis judged complete by TLC analysis (several hours)
extractionextracted with ethyl acetate
washThe ethyl acetate solution is washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated at reduced pressure

Sources & evidence

ORD record: ord-1c27b8bd615f453daa0a829294efdf96
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610728B2

Reaction notes

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