Trifluoroacetic acid → HCID 21105285, compound

HRID 1364967Notes

Reaction equation

HRID 1364967 reaction equation
[Br:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:11]([O:15][C:16](=[O:19])[CH2:17]Br)(C)(C)C.[H-].[Na+].[C:22]([OH:28])([C:24](F)(F)F)=[O:23]>CN(C=O)C>[Br:1][C:2]1[N:3]([CH2:24][C:22]([OH:28])=[O:23])[C:5]2[C:4]([C:10]=1[CH:9]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1)=[CH:9][CH:8]=[C:17]([C:16]([O:15][CH3:11])=[O:19])[CH:6]=2

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 118056312-bromo-1H-indole

Product 1

HCID 21105285HCID 21105285, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 2-bromoindole from example 2 was N-alkylated with tert-butylbromoacetate using NaH in DMF and the tert-butyl ester cleaved with TFA as described in example 6 to give the title compound of example 8 as a white solid.

Sources & evidence

ORD record
ord-129b403c4b2f49e4860492c46fd10ae8
Source dataset
uspto-grants-2011_02
Patent number
US07888363B2

Reaction notes

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