Ammonium Chloride → 2-(2-Ethoxycarbonylfuran-5-yl-methyl)-1-(4-fluorobenzyl)-5-methanesulfonylindole

HRID 1814124Notes

Reaction equation

HRID 1814124 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]([CH2:11][C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:16][CH:15]=3)=[CH:9][CH:10]=1)=[O:5])[CH3:2].[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1.[Cl-].[NH4+]>O1CCCC1.C([N-]C(C)C)(C)C.[Li+]>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]([CH2:11][C:12]2[N:13]([CH2:30][C:29]3[CH:32]=[CH:33][C:26]([F:25])=[CH:27][CH:28]=3)[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:16][CH:15]=3)=[CH:9][CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 680214-Fluorobenzyl bromideHCID 225044502-(2-Ethoxycarbonylfuran-5-yl-methyl)-5-methanesulfonylindole

Product 1

HCID 225044152-(2-Ethoxycarbonylfuran-5-yl-methyl)-1-(4-fluorobenzyl)-5-methanesulfonylindole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2724682Lithium diisopropylamideSolvent

Procedure

To a solution of the compound obtained in Example 30 (5) (0.0592 g) in tetrahydrofuran (2 ml), 2.0 M lithium diisopropylamide solution (0.0852 ml) was added dropwise at −78° C. and the mixture was stirred for 30 minutes. 4-Fluorobenzyl bromide (0.02 ml) was then added to the mixture, followed by stirring at the same temperature for 30 minutes. The reaction solution was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous NaCl solution, dried over anhydride magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel preparative thin-layer chromatography (hexane:ethyl acetate=1:1) to obtain 0.005 g of the desired product.

Workup

  1. stirringby stirring at the same temperature for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous NaCl solution
  4. dry with materialdried over anhydride magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was separated

Sources & evidence

ORD record
ord-818bcb71cd35456ab751bcaa0b2076c2
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

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