Water → HCID 57625532, compound

HRID 2390454Notes

Reaction equation

HRID 2390454 reaction equation
Br[CH2:2][CH2:3][Cl:4].[Br:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[CH:9]2.C([O-])([O-])=O.[Cs+].[Cs+].O>CS(C)=O>[Br:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:2][CH2:3][Cl:4])[N:10]=[CH:9]2

Participants

6

Reactant 4

HCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 10796Cesium carbonateHCID 7619295-bromo-1H-indazole

Product 1

HCID 57625532HCID 57625532, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
25 °C

Procedure

1-Bromo-2-chloroethane (2.9 mL, 35 mmol) was added to a suspension of 5-bromo-1H-indazole (4.302 g, 21.95 mmol) and Cs2CO3 (28.56 g, 87.81 mmol) in DMSO (50 mL) under N2. The resulting suspension was stirred at 25° C. for 6 h. H2O (50 mL) was added, and the resulting suspension was cooled in an ice bath. The suspension was filtered, and the solid was dried under reduced pressure to afford a pink powder. Flash chromatography on silica gel (19:1 to 5:2 hexanes/EtOAc) gave the title compound (3.094 g, 54%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 8.00 (br s, 1H), 7.90 (d, J=1.5 Hz, 1H), 7.50 (dd, J=9.0, 1.5 Hz, 1H), 7.38 (d, J=9.0 Hz, 1H), 4.68 (t, J=6.3 Hz, 2H), 3.98 (t, J=6.3 Hz, 2H).

Workup

  1. temperaturethe resulting suspension was cooled in an ice bath
  2. filtrationThe suspension was filtered
  3. customthe solid was dried under reduced pressure
  4. customto afford a pink powder

Sources & evidence

ORD record
ord-ccf2d1fe2c4348549de6699d5bf1c9e8
Source dataset
uspto-grants-2012_09
Patent number
US08273770B2

Reaction notes

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