tert-Butyl (2-(trifluoromethyl)phenyl)carbamate → lithium 2-(7-(trifluoromethyl)-1H-indol-2-yl)acetate

HRID 641594Notes

Reaction equation

HRID 641594 reaction equation
[F:1][C:2]([F:18])([F:17])C1C=CC=CC=1NC(=O)OC(C)(C)C.FC(F)(F)O[C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][C:26]([CH2:31][C:32]([O-:34])=[O:33])=[CH:25]2.[Li+:37].CC(C)([O-])C.[K+]>>[F:1][C:2]([F:18])([F:17])[C:29]1[CH:30]=[CH:22][CH:23]=[C:24]2[C:28]=1[NH:27][C:26]([CH2:31][C:32]([O-:34])=[O:33])=[CH:25]2.[Li+:37]

Participants

4

Reactant 3

HCID 15033883tert-Butyl (2-(trifluoromethyl)phenyl)carbamateHCID 23665647Potassium tert-butoxideHCID 68638606HCID 68638606, compound

Product 1

HCID 68638559lithium 2-(7-(trifluoromethyl)-1H-indol-2-yl)acetate

Procedure

The titled compound was prepared from tert-butyl 2-(trifluoromethyl)phenylcarbamate using the procedures described in Example 26, Steps 26b through 26h, except for the use of potassium tert-butoxide instead of potassium hexamethyldisilizane in step 26g. MS (ES+) detects free acid at 244 (M+H+).

Sources & evidence

ORD record
ord-0ea9e34240e14b308d76ffe5eb7ac2cc
Source dataset
uspto-grants-2010_04
Patent number
US07696205B2

Reaction notes

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