Trifluoroacetic acid → 1-(2-cyano-4-(2-methoxy-2-oxoethyl)phenyl)-1H-indole-5-carboxylic acid

HRID 1810101Notes

Reaction equation

HRID 1810101 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:5][C:4]=1[N:14]1[C:22]2[C:17](=[CH:18][C:19]([C:23]([O:25]C(C)(C)C)=[O:24])=[CH:20][CH:21]=2)[CH:16]=[CH:15]1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[C:7]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:5][C:4]=1[N:14]1[C:22]2[C:17](=[CH:18][C:19]([C:23]([OH:25])=[O:24])=[CH:20][CH:21]=2)[CH:16]=[CH:15]1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68515072tert-butyl 1-(2-cyano-4-(2-methoxy-2-oxoethyl)phenyl)-1H-indole-5-carboxylate

Product 1

HCID 685123251-(2-cyano-4-(2-methoxy-2-oxoethyl)phenyl)-1H-indole-5-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl 1-(2-cyano-4-(2-methoxy-2-oxoethyl)phenyl)-1H-indole-5-carboxylate (0.380 g, 0.973 mmol, in 2 ml of DCM was added 2 mL of TFA and the reaction stirred at ambient temperature under nitrogen. After 2 hours, the reaction was concentrated to give 1-(2-cyano-4-(2-methoxy-2-oxoethyl)phenyl)-1H-indole-5-carboxylic acid (0.320 g, 0.957 mmol, 98%). MS (APCI negative)=333.2 (M−1).

Workup

  1. concentrationthe reaction was concentrated

Sources & evidence

ORD record
ord-f211fd9739c547ff9759c6182a783014
Source dataset
uspto-grants-2013_01
Patent number
US08362056B2

Reaction notes

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