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

HRID 1280815Notes

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) was added to 7.82 g (24 mmol) cesium carbonate in 25 mL DMF and the mixture 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 was added and stirring maintained until the reaction was judged complete by TLC analysis (several hours). The mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried (MgSO4) and concentrated at reduced pressure to give 6.8 g of solid. Mass spectrum: 365

Workup

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

Sources & evidence

ORD record: ord-bd2d314d894b4cb18901d38a0e32777e
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451839B1

Reaction notes

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