6-Benzyloxy-5-fluoro-1H-indole-2-carboxylic acid methyl ester → HCID 69282929, compound

HRID 901096Notes

Reaction equation

HRID 901096 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([F:14])=[C:9]([O:15]CC1C=CC=CC=1)[CH:8]=2)=[O:4]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([F:14])=[C:9]([OH:15])[CH:8]=2)=[O:4]

Participants

4

Reactant 1

HCID 441851846-Benzyloxy-5-fluoro-1H-indole-2-carboxylic acid methyl ester

Product 1

HCID 69282929HCID 69282929, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 20.2 g (0.067 mol) 6-benzyloxy-5-fluoro-1H-indole-2-carboxylic acid methyl ester in 800 ml ethyl acetate was treated with 2 g (10%) Pd/C and hydrogenated at 1 bar for 2 h. After filtration and evaporation the residue was re-crystallized from ethyl acetate. The crystals were filtered off washed with diethyl ether and dried at 40° C. under vacuum to yield 10.9 g (74%) of the title compound as white crystals. MS (m/e): 208.1 (MH−, 100%).

Workup

  1. filtrationAfter filtration and evaporation the residue
  2. customwas re-crystallized from ethyl acetate
  3. filtrationThe crystals were filtered off
  4. washwashed with diethyl ether
  5. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-4ddb1ae972894daea1a9f2e7f50b5c8c
Source dataset
uspto-grants-2008_04
Patent number
US07361682B2

Reaction notes

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