Potassium Hydroxide → HCID 58056555, compound

HRID 555667Notes

Reaction equation

HRID 555667 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[NH:8][CH:7]=1.[Br:17][C:18]1[C:19]([CH3:28])=[C:20]([S:24](Cl)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1.[OH-].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[N:8]([S:24]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([Br:17])[C:19]=2[CH3:28])(=[O:25])=[O:26])[CH:7]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 446310013-Bromo-2-methylbenzene-1-sulfonyl chlorideHCID 58056522HCID 58056522, compound

Product 1

HCID 58056555HCID 58056555, compoundYield 59.72%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

Into a flask, 3-(5-fluoro-1H-indol-3-yl)-propionic acid methyl ester (3, 530.000 mg, 2.39572E-3 mol), 3-bromo-2-methyl-benzene sulfonyl chloride (4, 710.33 mg, 0.0026353 mol), 62.35 mL methylene chloride, 17 mL 50% KOH and a catalytic amount of tetra-n-butyl ammonium hydrogen sulfate were combined and stirred at room temperature for 48 hours. The organic layer was washed with saturated sodium bicarbonate, dried over MgSO4 and filtered. The organic layer was concentrated at reduced pressure to afford a tannish solid. Purification by flash chromatography using a gradient of 0-25% ethyl acetate in hexanes over 35 minutes yielded the desired compound (5, 650 mg, 59.72%). 1H NMR consistent with desired compound. MS(ESI) [M+H+]+==454.0, 456.0.

Workup

  1. washThe organic layer was washed with saturated sodium bicarbonate
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationThe organic layer was concentrated at reduced pressure
  5. customto afford a tannish solid
  6. customPurification by flash chromatography
  7. customover 35 minutes

Sources & evidence

ORD record
ord-65bc3deef02e43f980bff4bf4ce4d6d1
Source dataset
uspto-grants-2011_11
Patent number
US08053463B2

Reaction notes

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