3-(5-{(S)-1-[1-(4-Methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-3-yl)-indole-1-carboxylic Acid Tert-butyl Ester → 3-((S)-5-Pyrrolidin-2-yl-pyridin-3-yl)-1H-indole

HRID 1667630Notes

Reaction equation

HRID 1667630 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[CH:18]=[N:19][CH:20]=[C:21]([C@@H:23]3[CH2:27][CH2:26][CH2:25][N:24]3C(C3C=CC(OC)=CC=3)C)[CH:22]=2)=[CH:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O>[NH:24]1[CH2:25][CH2:26][CH2:27][C@H:23]1[C:21]1[CH:22]=[C:17]([C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:8][CH:9]=2)[CH:18]=[N:19][CH:20]=1

Participants

3

Reactant 1

HCID 581119913-(5-{(S)-1-[1-(4-Methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-3-yl)-indole-1-carboxylic Acid Tert-butyl Ester

Product 1

HCID 581118843-((S)-5-Pyrrolidin-2-yl-pyridin-3-yl)-1H-indoleYield 49%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-(5-{(S)-1-[1-(4-Methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-3-yl)-indole-1-carboxylic acid tert-butyl ester 5 (300 mg, 0.63 mmole) in 4 mL of TFA was heated at 100° C. in a microwave reactor for 20 minutes. The result solution was concentrated to remove TFA as much as possible. The residue was purified by HPLC (Column: Waters Sunfire, 30×30 mm; Mobile phase: CH3CN 15% H2O 85% with 0.1% TFA to CH3CN 60% H2O 40% with 0.1% TFA by gradient in 11 minutes; Flow rate 45 mL/minute; Detector: 215 nm UV) to give 3-((S)-5-Pyrrolidin-2-yl-pyridin-3-yl)-1H-indole 6 (78 mg, yield 49%) as white solid.

Workup

  1. concentrationThe result solution was concentrated
  2. customto remove TFA as much as possible
  3. customThe residue was purified by HPLC (Column: Waters Sunfire, 30×30 mm; Mobile phase: CH3CN 15% H2O 85% with 0.1% TFA to CH3CN 60% H2O 40% with 0.1% TFA by gradient in 11 minutes; Flow rate 45 mL/minute; Detector: 215 nm UV)

Sources & evidence

ORD record
ord-fb61cc61b5b04b42b91ac866bfca3efe
Source dataset
uspto-grants-2011_10
Patent number
US08044209B2

Reaction notes

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