Pyridine → HCID 17882414, compound

HRID 369404Notes

Reaction equation

HRID 369404 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[N:11]([CH3:23])[C:12]([C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:13][CH:14]=1)[NH2:5].N1C=CC=CC=1.[C:30]([O:33][CH2:34][CH2:35][S:36](Cl)(=[O:38])=[O:37])(=[O:32])[CH3:31]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([NH:5][S:36]([CH2:35][CH2:34][O:33][C:30](=[O:32])[CH3:31])(=[O:38])=[O:37])[CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[N:11]([CH3:23])[C:12]([C:15](=[O:22])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 131390002-(chlorosulfonyl)ethyl acetateHCID 70102005HCID 70102005, compound

Product 1

HCID 17882414HCID 17882414, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Fluoro-4-[5-benzoyl-1-methyl-1H-pyrrol-2-ylmethyl]aniline (0.75 g, 2.43 mmol) [prepared as described in Example 1, but substituting ethyl 1,4-dimethylpyrrole-2-acetate with methyl 1-methylpyrrole-2-acetate in Step (a)], and pyridine (0.39 ml, 4.88 mmol) were dissolved in methylene chloride (8 ml). 2-Acetoxyethanesulfonyl chloride (681 mg, 3.65 mmol) was added to the solution and after 15 min, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated to dryness. Purification of the residue by flash chromatography (hexane-ethyl acetate, 3:2) gave N-{3-fluoro-4-[5-benzoyl-1-methyl-1H-pyrrol-2-ylmethyl]phenyl}-2-(acetoxy)ethanesulfonamide, (643 mg, 58%) as a solid. ##STR58##

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customPurification of the residue by flash chromatography (hexane-ethyl acetate, 3:2)

Sources & evidence

ORD record
ord-f0a9d95e252e48d485a9f89fa3210c60
Source dataset
uspto-grants-2000_10
Patent number
US06136844

Reaction notes

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