Potassium Carbonate → 3-Amino-6-chloro-2-(3-methoxybenzoyl)indole

HRID 379728Notes

Reaction equation

HRID 379728 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[N:4](C(OCC)=O)[C:3]=1[C:17](=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1.C([O-])([O-])=O.[K+].[K+]>C(O)C>[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:17](=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 183677433-Amino-6-chloro-1-ethoxycarbonyl-2-(3-methoxybenzoyl)indole

Product 1

HCID 183680283-Amino-6-chloro-2-(3-methoxybenzoyl)indoleYield 68.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-amino-6-chloro-1-ethoxycarbonyl-2-(3-methoxybenzoyl)indole (step 1, 998 mg, 2.68 mmol) and K2CO3 (3.70 g, 26.8 mmol) in 70% aqueous ethanol (45 ml) was refluxed for 6.5 h and then cooled to room temperature. The mixture was concentrated to ca. 20 ml, diluted with ethyl acetate (150 ml), and the organic layer washed with water (50 ml×2) and dried (Na2SO4). After removal of solvent the residue was purified by flash chromatography eluting with ethyl acetate/hexane (1:4) to afford 549 mg (68%) of the title compound as a syrup. 1H-NMR (CDCl3) δ: 7.62 (1H, br s), 7.55-7.30 (5H, m), 7.23 (1H, d, J=1.5 Hz), 7.10 (1H, ddd, J=1.1, 2.6, and 8.1 Hz), 5.60 (2H, br s), 3.88 (3H, s)

Workup

  1. temperaturewas refluxed for 6.5 h
  2. concentrationThe mixture was concentrated to ca. 20 ml
  3. additiondiluted with ethyl acetate (150 ml)
  4. washthe organic layer washed with water (50 ml×2)
  5. dry with materialdried (Na2SO4)
  6. customAfter removal of solvent the residue
  7. customwas purified by flash chromatography
  8. washeluting with ethyl acetate/hexane (1:4)

Sources & evidence

ORD record
ord-b6601340f803422ba1b057f031bb0458
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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