Cesium carbonate → HCID 68770240, compound

HRID 1947455Notes

Reaction equation

HRID 1947455 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O-:13])=[O:12])=[CH:5]2.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:21]1[S:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1>CS(C)=O>[S:22]1[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=[C:21]1[O: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:12])=[CH:5]2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 119872-ChlorobenzothiazoleHCID 178524047HCID 178524047, compound

Product 1

HCID 68770240HCID 68770240, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 5-hydroxyindole-2-carboxylate (5 g, 28.2 mmol), Cs2CO3 (20 g, 62.1 mmol) in DMSO (56 mL) was added 2-chlorobenzthiazole (3.5 mL, 4.8 g, 28.2 mmol) and the resulting reaction mixture was heated (70° C., 2 d). The reaction mixture was cooled (rt) and partitioned with H2O and EtOAc (50 mL each). The aqueous layer was treated with concentrated HCl to form a solid. The suspension was filtered and the solid washed with H2O and dried in vacuo to provide the title compound as a brown solid (7.55 g, 86%). 1H NMR (500 MHz, DMSO-d6): 12.03 (s, 1H), 7.88 (d, J=7.5, 1H), 7.73 (d, J=2.4, 1H), 7.67 (d, J=7.5, 1H), 7.55 (d, J=8.9, 1H), 7.43-7.40 (m, 1H), 7.31-7.28 (m, 2H), 7.15 (d, J=1.4, 1H), the CO2H proton was not detected.

Workup

  1. customthe resulting reaction mixture
  2. temperatureThe reaction mixture was cooled (rt)
  3. custompartitioned with H2O and EtOAc (50 mL each)
  4. additionThe aqueous layer was treated with concentrated HCl
  5. customto form a solid
  6. filtrationThe suspension was filtered
  7. washthe solid washed with H2O
  8. customdried in vacuo

Sources & evidence

ORD record
ord-d09d86ce5be74b389d2af3ec79123ccd
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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