Ammonium formate → 4-Amino-5-methoxy-1-methylindole-2-carboxylic acid methyl ester

HRID 968478Notes

Reaction equation

HRID 968478 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:19])[C:7]2[C:12]([CH:13]=1)=[C:11]([N+:14]([O-])=O)[C:10]([O:17][CH3:18])=[CH:9][CH:8]=2)=[O:4].C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:19])[C:7]2[C:12]([CH:13]=1)=[C:11]([NH2:14])[C:10]([O:17][CH3:18])=[CH:9][CH:8]=2)=[O:4]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 206071685-Methoxy-1-methyl-4-nitroindole-2-carboxylic acid methyl ester

Product 1

HCID 206071674-Amino-5-methoxy-1-methylindole-2-carboxylic acid methyl esterYield 67.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of 9 (1.0g, 3.78 mmol) in anhydrous methanol (90 mL) was added 10% Pd/C (150 mg) suspended in anhydrous methanol (15 mL) followed by ammonium formate (1.10 g, 17.4 mmol). The reaction mixture was stirred for 1 h, filtered through celite and the methanol removed. The residue was taken up in CH2Cl2/H2O and extracted with CH2Cl2 (3×). The combined organic layers were dried over Na2SO4 and evaporated to afford 10 (595 mg, 67%) as a brown solid which was used without further purification; 1H NMR (CDCl3): δ 7.21 (1H, s), 7.06 (1H, d), 6.72 (1H, d), 4.01 (3H, s), 3.90 (3H, s), 3.88 (3H, s).

Workup

  1. filtrationfiltered through celite
  2. customthe methanol removed
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-dcfe474719944717ba8377a2f223018b
Source dataset
uspto-grants-2007_12
Patent number
US07304046B2

Reaction notes

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