Cesium carbonate → HCID 68770255, compound

HRID 1947458Notes

Reaction equation

HRID 1947458 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([OH:14])[CH:8]=2)=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:22]1[S:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([O:14][C:22]1[S:23][C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[N:26]=1)[CH:8]=2)=[O:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 119872-ChlorobenzothiazoleHCID 10535709methyl 6-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 68770255HCID 68770255, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution 6-hydroxy-1H-indole-2-carboxylic acid methyl ester (4.7 g, 24.5 mmol) in DMF (250 mL) was added Cs2CO3 (8.0 g, 24.5 mmol) followed by 2-chloro-benzothiazole (3.0 mL, 4.2 g, 24.5 mmol) and the reaction mixture was heated (70° C., 12 h). The reaction mixture was cooled (rt) and concentrated in vacuo. The resulting residue was partitioned between EtOAc (200 mL) and brine (100 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2×300 mL). The organic layer was dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using EtOAc:hexane (0-40%) to provide the title compound as a colorless foam (3.6 g, 45%). MS (ESI): mass calcd. for O17H12N2O3S, 324.1; m/z found, 325.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 9.17 (s, 1H), 7.77-7.63 (m, 3H), 7.46-7.42 (m, 1H), 7.42-7.34 (m, 1H), 7.30-7.26 (m, 1H), 7.23-7.19 (m, 1H), 7.14 (dd, J=8.7, 2.1, 1H), 3.94 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled (rt)
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was partitioned between EtOAc (200 mL) and brine (100 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with EtOAc (2×300 mL)
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-356122dde72b4ddd991c0207a4f382d7
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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