Formic Acid → 1-Methyl-1H-indole-7-carboxylic acid

HRID 380471Notes

Reaction equation

HRID 380471 reaction equation
C([O:8][C:9]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[N:18]([CH3:20])[CH:17]=[CH:16]2)=[O:10])C1C=CC=CC=1.C(O)=O>CO.[Pd]>[CH3:20][N:18]1[C:19]2[C:15](=[CH:14][CH:13]=[CH:12][C:11]=2[C:9]([OH:10])=[O:8])[CH:16]=[CH:17]1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 18388396Benzyl-1-methylindole-7-carboxylate

Product 1

HCID 183883621-Methyl-1H-indole-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.65 g (0.25 mmol) of benzyl-1-methylindole-7-carboxylate (Step B) and 0.035 g of 10% Pd/C in 4 mL of a solution of 4.4% HCO2H in MeOH was stirred for 2 h at rt. The reaction mixture was filtered though a thin pad of celite and concentrated to give the title compound. 1H NMR (CDCl3) δ4.00 (s, 3H), 6.61 (d, 1H, J=3 Hz), 7.11 (d, 1H, J=3 Hz), 7.18 (t, 1H, J=8 Hz), 7.87 (d, 1H, J=8 Hz), 7.91 (d, 1H, J=8 Hz);

Workup

  1. filtrationThe reaction mixture was filtered though a thin pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7fd79f8e079043328b13b6fa665101de
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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