Trifluoroacetic acid → 3-((S)-5-Pyrrolidin-2-yl-pyridin-3-yl)-1H-indole
Reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C@@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C@@H](C2C=CC(OC)=CC=2)C)[CH:7]=1.[C:23](O)([C:25](F)(F)F)=O>>[NH:9]1[CH2:10][CH2:11][CH2:12][C@H:8]1[C:6]1[CH:7]=[C:2]([C:2]2[C:23]3[C:25](=[CH:5][CH:6]=[CH:8][CH:12]=3)[NH:4][CH:3]=2)[CH:3]=[N:4][CH:5]=1Participants
3
Procedure
A solution of 3-Bromo-5-{(S)-1-[(R)-1-(4-methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridine 3 (3.64 g, 10.0 mmole) in 5 mL of TFA was heated at 120° C. in a microwave reactor for 30 minutes. The resulting solution was concentrated to remove TFA. The residue was dissolved in 150 mL of CH2Cl2 and basicfied by 5 mL of saturated NaHCO3. The solution was washed by 2×10 mL of water, dried over Na2SO4 and concentrated to give 3-((S)-5-Pyrrolidin-2-yl-pyridin-3-yl)-1H-indole 4 (2.4 g, crude) as deep brown gum without further purification for the next step reaction.
Workup
- concentrationThe resulting solution was concentrated
- customto remove TFA
- dissolutionThe residue was dissolved in 150 mL of CH2Cl2
- washThe solution was washed by 2×10 mL of water
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4a10a14555d74537a8b5849015d150e6
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08044209B2
Reaction notes
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