Cesium carbonate → HCID 71062895, compound

HRID 576577Notes

Reaction equation

HRID 576577 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-70841f857db14b16870f7403aedb650e
Source dataset
uspto-grants-2015_05
Patent number
US09040517B2

Reaction notes

Loading…