Potassium Carbonate → HCID 66765708, compound

HRID 1466823Notes

Reaction equation

HRID 1466823 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([S:11][C:12]2[C:20]3[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH3:22])[CH:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[C:31]1[CH:32]=[N:33][S:34][CH:35]=1>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([S:11][C:12]2[C:20]3[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=3)[N:14]([C:31]3[CH:32]=[N:33][S:34][CH:35]=3)[C:13]=2[CH3:22])[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 52003584-Bromo-isothiazoleHCID 667654983-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid ethyl ester

Product 1

HCID 66765708HCID 66765708, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
145 °C

Procedure

3-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid ethyl ester (0.250 g, 0.723 mmol) was combined with CuO (0.118 g, 1.48 mmol), potassium carbonate (0.130 g, 0.941 mmol) and 4-bromoisothiazole (0.250 g, 1.52 mmol) in pyridine (2 mL) and the reaction was heated to 145° C. overnight. After cooling the reaction was partitioned between H2O and DCM and the aqueous layer was extracted with DCM. The combined organics were dried over MgSO4 and concentrated then submitted to silica gel chromatography (0-20% EtOAc in hexanes) to yield the title compound.

Workup

  1. temperatureAfter cooling the reaction
  2. customwas partitioned between H2O and DCM
  3. extractionthe aqueous layer was extracted with DCM
  4. dry with materialThe combined organics were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a978a389e396497faa69b7ff65be2d1b
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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