3,3,3-Trifluoropropane-1-sulfonyl chloride → 3,3,3-Trifluoropropane-1-sulfonic acid 4-[1-(2,4-dichlorophenyl)-3-methyl-4-oxo-5-piperidin-1-yl-4,5-dihydro-1H-pyrrolo[3,2-c]pyridin-2-yl]phenyl ester

HRID 2102875Notes

Reaction equation

HRID 2102875 reaction equation
[F:1][C:2]([F:10])([F:9])[CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[N:19]1[C:27]2[CH:26]=[CH:25][N:24]([N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[C:23](=[O:34])[C:22]=2[C:21]([CH3:35])=[C:20]1[C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=1>N1C=CC=CC=1>[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[N:19]1[C:27]2[CH:26]=[CH:25][N:24]([N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[C:23](=[O:34])[C:22]=2[C:21]([CH3:35])=[C:20]1[C:36]1[CH:37]=[CH:38][C:39]([O:42][S:5]([CH2:4][CH2:3][C:2]([F:10])([F:9])[F:1])(=[O:7])=[O:6])=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 27611773,3,3-Trifluoropropane-1-sulfonyl chloride2×HCID 578035911-(2,4-dichlorophenyl)-2-(4-hydroxyphenyl)-3-methyl-5-piperidin-1-yl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one

Product 1

HCID 166660843,3,3-Trifluoropropane-1-sulfonic acid 4-[1-(2,4-dichlorophenyl)-3-methyl-4-oxo-5-piperidin-1-yl-4,5-dihydro-1H-pyrrolo[3,2-c]pyridin-2-yl]phenyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3,3,3-Trifluoro-propane-1-sulfonyl chloride (100 mg, 0.509 mmol) was added to 1-(2,4-dichlorophenyl)-2-(4-hydroxyphenyl)-3-methyl-5-piperidin-1-yl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one (74 mg, 0.158 mmol) dissolved in pyridine (5 ml) at 0° C. The reaction was continued at 0° C. for 1 h and 15 min and then at rt. After 15 min at rt more 3,3,3-trifluoro-propane-1-sulfonyl chloride (260 mg, 1.323 mmol) was added. After 15 min the solvent was evaporated. Purified by flash chromatography (20-100% EtOAc in toluene) to yield the title compound as a white solid after evaporation (24 mg, 24%).

Workup

  1. customat rt
  2. customAfter 15 min the solvent was evaporated
  3. customPurified by flash chromatography (20-100% EtOAc in toluene)

Sources & evidence

ORD record
ord-85da6720e14244c1ac09b3cff0f4fbd1
Source dataset
uspto-grants-2009_08
Patent number
US07576095B2

Reaction notes

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