Réaction #44907

Équation de réaction

potassium phosphate monobasic

sodium chlorite

2-methyl-2-butene

potassium phosphate monobasic

sodium chlorite

1-benzyl-2-methyl-5-nitro-1H-indole-3-carboxaldehyde

Compound 50

1-benzyl-2-methyl-5-nitro-1H-indole-3-carboxaldehyde

→

1-benzyl-2-methyl-5-nitro-1H-indole-3-carboxylic acid

Rendement 101.1%

Solvants

acetonitrile

tert-butanol

H2O

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred at room temperature for 24 h
2. 2
   AutreThe solvent was removed under reduced pressure
3. 3
   LavageThe residue solid was washed with H2O (×3)
4. 4
   Filtrationfiltered
5. 5
   workup.DISSOLUTIONdissolved in acetone
6. 6
   Filtrationfiltered

Mode opératoire

To a suspension of 1-benzyl-2-methyl-5-nitro-1H-indole-3-carboxaldehyde (Compound 50, 150 mg, 0.51 mmol) in acetonitrile (6 ml), tert-butanol (6 ml) and H2O (6 ml) was added 2-methyl-2-butene (4 ml), potassium phosphate monobasic (1.4 g, 10.2 mmol), sodium chlorite (80%, 1.15 g, 10.2 mmol). The mixture was stirred at room temperature for 20 h, more potassium phosphate monobasic (0.35 g, 2.6 mmol) and sodium chlorite (80%, 0.29 g, 2.6 mmol) were added and stirred at room temperature for 24 h. The solvent was removed under reduced pressure. The residue solid was washed with H2O (×3) and filtered, dissolved in acetone and filtered to yield 1-benzyl-2-methyl-5-nitro-1H-indole-3-carboxylic acid (Compound 51) as a yellow powder (160 mg, 100%). 1H-NMR (ACETONE-d6) δ 2.83 (s, 3 H), 5.68 (s, 2 H), 7.06-7.15 (m, 2 H), 7.25-7.41 (m, 3 H), 7.68 (d, J=9.1 Hz, 1 H), 8.10 (dd, J =9.1, 2.3 Hz, 1 H), 9.11 (d, J=2.3 Hz, 1 H).

Source