5-(2-Methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester → HCID 22311862, compound

HRID 966537Notes

Reaction equation

HRID 966537 reaction equation
C([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][O:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH:18]=2)[NH:13][C:12]=1[CH3:27])=[O:10])C1C=CC=CC=1>C1COCC1.[Pd]>[CH3:26][S:23]([O:22][CH2:21][CH2:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([CH3:27])=[C:11]2[C:9]([OH:10])=[O:8])(=[O:24])=[O:25]

Participants

4

Reactant 1

HCID 233938525-(2-Methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

Product 1

HCID 22311862HCID 22311862, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(2-methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (1.22 g, 3.15 mmol, Example 56, Step D) in dry THF (10 mL) was added 20% palladium on carbon (1 g). The mixture was stirred under hydrogen atmosphere at room temperature overnight. The TLC showed the reaction was complete. The mixture was filtered and the filtrate was concentrated in vacuo to give a residue, which was purified by chromatography (50%-100% ethyl acetate in hexanes) to give 450 mg (48%) of the desired product as a white solid: mp 157-158° C.; MS(APCI−): m/z 296.0 (M−H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto give a residue, which
  4. customwas purified by chromatography (50%-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-4dd4ad530441406cb66e534386475dc1
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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