1-(5-{(S)-1-[(R)-1-(4-Methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-3-yl)-1H-indole-4-carboxylic acid ethyl ester → 1-((S)-5-Pyrrolidin-2-yl-pyridin-3-yl)-1H-indole-4-carboxylic acid ethyl ester

HRID 880610Notes

Reaction equation

HRID 880610 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH:8]=[CH:9][N:10]([C:15]3[CH:16]=[N:17][CH:18]=[C:19]([C@@H:21]4[CH2:25][CH2:24][CH2:23][N:22]4[C@@H](C4C=CC(OC)=CC=4)C)[CH:20]=3)[C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:5])[CH3:2]>C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH:8]=[CH:9][N:10]([C:15]3[CH:16]=[N:17][CH:18]=[C:19]([C@@H:21]4[CH2:25][CH2:24][CH2:23][NH:22]4)[CH:20]=3)[C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 679743931-(5-{(S)-1-[(R)-1-(4-Methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-3-yl)-1H-indole-4-carboxylic acid ethyl ester

Product 1

HCID 679742211-((S)-5-Pyrrolidin-2-yl-pyridin-3-yl)-1H-indole-4-carboxylic acid ethyl esterYield 86.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1-(5-{(S)-1-[(R)-1-(4-methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-3-yl)-1H-indole-4-carboxylic acid ethyl ester (I-1A-1a: 5.0 g, 11 mmol) in TFA (15 mL) was heated in a microwave tube at 100° C. for 30 minutes. The resulting mixture was concentrated under reduced pressure to give a di-TFA salt of the titled compound as a red oil (3.2 g) which was used directly in the next step without purification.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5407d041322744ea8fa1d581f1f184fa
Source dataset
uspto-grants-2015_03
Patent number
US08993523B2

Reaction notes

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