3-Fluorobenzenesulfonyl Chloride → HCID 67440735, compound

HRID 1801366Notes

Reaction equation

HRID 1801366 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:17]([CH3:19])([CH3:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=2)[NH:9]1.[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.ClCCl>[F:24][C:25]1[CH:26]=[C:27]([S:31]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH:8]2[C:17]([CH3:18])([CH3:19])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=3)[NH:9]2)(=[O:33])=[O:32])[CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 67441977HCID 67441977, compound

Product 1

HCID 67440735HCID 67440735, compoundYield 131.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of methyl 2-(2-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (1.0 g, 3.22 mmol, 1.0 eq.) in pyridine (5 mL) and dichloro methane (20 mL) at 0° C. was dropwise a solution of 3-fluorobenzene-1-sulfonyl chloride (940 mg, 4.83 mmol, 1.5 eq.) in dichloromethane (30 mL). The mixture was stirred at room temperature for 6 h. Thin layer chromatography and LC-MS showed reaction completed. The mixture was quenched with 50 mL water and extracted with ethyl acetate (100 mL×3). The combined organic layers were dried over anhydrous sodium sulfate and evaporated to afford 1.987 g of methyl 2-(2-(3-fluorophenylsulfonamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (pyridine included) as light yellow solid, which was used in next step without further purification.

Workup

  1. customat 0° C.
  2. customreaction
  3. customThe mixture was quenched with 50 mL water
  4. extractionextracted with ethyl acetate (100 mL×3)
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-919903bd5f294ae7b10234bac5430e8d
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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