Potassium Carbonate → HCID 59334973, compound

HRID 1517940Notes

Reaction equation

HRID 1517940 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.[Cl:14][C:15]1[CH:16]=[C:17]([S:22]([N:25]([CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:26]2[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=2)[NH:31][CH2:30][CH2:29]3)(=[O:24])=[O:23])[CH:18]=[C:19]([Cl:21])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>S(Cl)(Cl)=O.ClCCl.CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:31]1[C:32]3[C:28](=[CH:27][C:26]([N:25]([CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[S:22]([C:17]4[CH:18]=[C:19]([Cl:21])[CH:20]=[C:15]([Cl:14])[CH:16]=4)(=[O:24])=[O:23])=[CH:34][CH:33]=3)[CH2:29][CH2:30]1)=[O:13])=[CH:5]2

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 59334895HCID 59334895, compound

Product 1

HCID 59334973HCID 59334973, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
80 °C

Procedure

55 mg 5-chloro-1H-indol-2-carboxylic acid are dissolved in 2 ml of thionyl chloride and heated to 80° C. for 1 hour. The solvent is eliminated in vacuo and the residue is twice combined with dichloromethane and the latter is eliminated again in vacuo. The residue is taken up in 5 ml dichloromethane and the solution is added dropwise to a mixture of 100 mg tert.butyl [(3,5-dichloro-phenylsulphonyl)-(2,3-dihydro-1H-indol-5-yl)-amino]-acetate and 60 mg potassium carbonate in 2 ml dimethylformamide. The mixture is stirred for 2 hours at ambient temperature, diluted with ethyl acetate and washed with 1 N HCl and saturated sodium chloride solution. After drying with magnesium sulphate the solvents are eliminated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 10:1 to 1:2).

Workup

  1. washwashed with 1 N HCl and saturated sodium chloride solution
  2. dry with materialAfter drying with magnesium sulphate the solvents
  3. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 10:1 to 1:2)

Sources & evidence

ORD record
ord-80712e4827204cb99ba9826d4f9bae86
Source dataset
uspto-grants-2012_07
Patent number
US08232312B2

Reaction notes

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