3-Fluorobenzenesulfonyl Chloride → HCID 67440485, compound

HRID 1801337Notes

Reaction equation

HRID 1801337 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]([CH3:20])([CH3:19])[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:21]([OH:23])=[O:22])[CH:15]=3)[NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[F:24][C:25]1[CH:26]=[C:27]([S:31](Cl)(=[O:33])=[O:32])[CH:28]=[CH:29][CH:30]=1>N1C=CC=CC=1>[F:8][C:7]1[CH:6]=[CH:5][C:4]([CH:9]2[C:18]([CH3:19])([CH3:20])[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:21]([OH:23])=[O:22])[CH:15]=3)[NH:10]2)=[CH:3][C:2]=1[NH:1][S:31]([C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([F:24])[CH:26]=1)(=[O:33])=[O:32]

Participants

4

Reactant 2

HCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 67443041HCID 67443041, compound

Product 1

HCID 67440485HCID 67440485, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To an ice-cold mixture of 2-(3-amino-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid (0.19 mmol, 1.0 eq.) in pyridine (5 mL) was added 3-fluorobenzene-1-sulfonyl chloride (0.29 mmol, 1.5 eq.) under nitrogen. Then the reaction mixture was stirred at room temperature for two hours. Thin layer chromatography and LC-MS indicated that the starting material was consumed completely. The reaction was quenched with 20 mL water extracted with ethyl acetate (20 mL×2). The combined organic layers were concentrated and the residue was purified by column chromatography (petroleum ether/ethyl acetate=1:1) to afford 2-(4-fluoro-3-(3-fluorophenylsulfonamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a pale yellow solid; Yield: 65%; MS (ESI+APCI) M+1=473.

Workup

  1. customwas consumed completely
  2. customThe reaction was quenched with 20 mL water
  3. extractionextracted with ethyl acetate (20 mL×2)
  4. concentrationThe combined organic layers were concentrated
  5. customthe residue was purified by column chromatography (petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-4aa3c06822164f2bb4b559c20ae9bd06
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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