Potassium Carbonate → 6-Chloro-2-(4-chloropyridine-2-carbonyl)-3-(2-hydroxyisobutyrylamino)indole

HRID 379868Notes

Reaction equation

HRID 379868 reaction equation
C([O:4][C:5]([CH3:29])([CH3:28])[C:6]([NH:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[NH:11][C:10]=1[C:19]([C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][N:22]=1)=[O:20])=[O:7])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.CS(C)=O.O.C(OCC)C>[Cl:18][C:14]1[CH:13]=[C:12]2[C:17]([C:9]([NH:8][C:6](=[O:7])[C:5]([OH:4])([CH3:29])[CH3:28])=[C:10]([C:19]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][N:22]=3)=[O:20])[NH:11]2)=[CH:16][CH:15]=1

Participants

7

Reactant 2

HCID 11430Potassium CarbonateHCID 183681673-(2-Acetoxyisobutyrylamino)-6-chloro-2-(4-chloropyridine-2-carbonyl)indole

Product 1

HCID 183678116-Chloro-2-(4-chloropyridine-2-carbonyl)-3-(2-hydroxyisobutyrylamino)indoleYield 45.8%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 3-(2-acetoxyisobutyrylamino)-6-chloro-2-(4-chloropyridine-2-carbonyl)indole (Example 360, 251.4 mg, 0.5789 mmol) in methanol (8 ml) and DMSO (20 ml) was added potassium carbonate (45.0 mg, 0.3259 mmol) in water (1 ml) at room tempetature. After stirring for 30 h, the mixture was diluted with diethyl ether (150 ml), and then washed with water (25 ml×3), brine (25 ml) and dried (MgSO4). Removal of solvent gave a crystalline residue, which was recrystallized from ethyl acetate to afford 103.9 mg (45.8%) of the title compound.

Workup

  1. washwashed with water (25 ml×3), brine (25 ml)
  2. dry with materialdried (MgSO4)
  3. customRemoval of solvent
  4. customgave a crystalline residue, which
  5. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-25503e18c1874510a0b05d81a1b559af
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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