Cesium carbonate → HCID 71062895, compound

HRID 921010Notes

Reaction equation

HRID 921010 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:2]1[S:3][CH:4]=[CH:5][N:6]=1)[CH:12]=[CH:11]2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 249055-BromoindoleHCID 764302-Bromothiazole

Product 1

HCID 71062895HCID 71062895, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2-Bromo thiazole (0.837 g, 5.10 mmol) was added to a solution of 5-bromo indole (1 g, 5.10 mmol) in DMF (15 mL) followed by cesium carbonate (3.32 g, 10.20 mmol), and the mixture was stirred at 90° C. for 12 h. Insoluble solids were filtered off, the filtrate was concentrated and partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over sodium sulphate, and filtered. The filtrate was concentrated under reduced pressure and purified by flash chromatography using 5% ethyl acetate in pet ether to afford title compound (0.75 g, 52.7%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.24 (d, J=8.8 Hz, 1H), 7.77 (d, J=2.0 Hz, 1H), 7.62 (dd, J1=3.2 Hz, J2=10.4 Hz, 2H), 7.45 (dd, J1=2.0 Hz, J2=8.8 Hz, 1H), 7.08 (d, J=3.6 Hz, 1H), 6.66 (d, J=4.0 Hz, 1H).

Workup

  1. filtrationInsoluble solids were filtered off
  2. concentrationthe filtrate was concentrated
  3. custompartitioned between ethyl acetate and water
  4. customOrganic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. custompurified by flash chromatography

Sources & evidence

ORD record
ord-201455dd72ca466e928fe614c59730a6
Source dataset
uspto-grants-2016_03
Patent number
US09273069B2

Reaction notes

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