Triethylamine → 3,3,3-Trifluoropropane-1-sulfonic acid 4-[1-(2-chlorophenyl)-3-methyl-4-oxo-5-piperidin-1-yl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-yl]phenyl ester

HRID 254335Notes

Reaction equation

HRID 254335 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[CH2:15][CH2:14][N:13]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:12](=[O:23])[C:11]=2[C:10]([CH3:24])=[C:9]1[C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1.C(N(CC)CC)C.[F:39][C:40]([F:48])([F:47])[CH2:41][CH2:42][S:43](Cl)(=[O:45])=[O:44]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[CH2:15][CH2:14][N:13]([N:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)[C:12](=[O:23])[C:11]=2[C:10]([CH3:24])=[C:9]1[C:25]1[CH:26]=[CH:27][C:28]([O:31][S:43]([CH2:42][CH2:41][C:40]([F:48])([F:47])[F:39])(=[O:45])=[O:44])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27611773,3,3-Trifluoropropane-1-sulfonyl chlorideHCID 166661641-(2-Chlorophenyl)-2-(4-hydroxyphenyl)-3-methyl-5-piperidin-1-yl-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridine-4-one

Product 1

HCID 160433293,3,3-Trifluoropropane-1-sulfonic acid 4-[1-(2-chlorophenyl)-3-methyl-4-oxo-5-piperidin-1-yl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-yl]phenyl esterYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-chlorophenyl)-2-(4-hydroxyphenyl)-3-methyl-5-piperidin-1-yl-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridine-4-one (0.54 g, 1.24 mmol) in dichloromethane (30 ml) at 0° C. was added triethylamine (0.20 ml, 1.50 mmol) followed by 3,3,3-trifluoropropane sulfonyl chloride (295 mg, 1.50 mmol). The reaction mixture was subsequently stirred at room temperature for 2.5 hours. Concentration and purification by flash chromatography (heptane:EtOAc gradient) afforded 65 mg (9%) of the title compound as a colorless solid.

Workup

  1. concentrationConcentration and purification by flash chromatography (heptane:EtOAc gradient)

Sources & evidence

ORD record
ord-1776d64b0fbc42e9abd3d8eda649e747
Source dataset
uspto-grants-2011_01
Patent number
US07875626B2

Reaction notes

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