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Piperidine → 2-(5-fluoro-2-methyl-3-(2-(piperidin-1-ylsulfonyl)benzyl)-1H-indol-1-yl)acetic acid ethyl ester

HRID 1919852
Notes
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Reaction equation

HRID 1919852 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([O:9][C:10](=[O:34])[CH2:11][N:12]1[C:20]2[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=2)[C:14]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29](Cl)(=[O:31])=[O:30])=[C:13]1[CH3:33])[CH3:8]>N1C=CC=CC=1.O>[CH2:7]([O:9][C:10](=[O:34])[CH2:11][N:12]1[C:20]2[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=2)[C:14]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:31])=[O:30])=[C:13]1[CH3:33])[CH3:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 8082PiperidineHCID 86633020ethyl 2-(3-(2-(chlorosulfonyl)benzyl)-5-fluoro-2-methyl-1H-indol-1-yl)acetate

Product 1

HCID 674907462-(5-fluoro-2-methyl-3-(2-(piperidin-1-ylsulfonyl)benzyl)-1H-indol-1-yl)acetic acid ethyl esterYield 72.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049
Pyridine
Solvent

Procedure

To a stirred solution of piperidine (0.36 mL, 3.6 mmol) in pyridine (50 mL) was added 2-(3-(2-(chlorosulfonyl)benzyl)-5-fluoro-2-methyl-1H-indol-1-yl)acetic acid ethyl ester (1.53 g, 3.6 mmol), and the resulting solution stirred at room temperature for 18 h. The mixture was then diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated copper sulfate solution (×3), dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford 2-(5-fluoro-2-methyl-3-(2-(piperidin-1-ylsulfonyl)benzyl)-1H-indol-1-yl)acetic acid ethyl ester (1.23 g, 2.60 mmol, 72%) as a yellow oil, which was used in the next step without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated copper sulfate solution (×3)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-5f91b08945eb46e8b61cf35d885a5a0e
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08168673B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes