Sodium Carbonate → HCID 178434330, compound

HRID 1880380Notes

Reaction equation

HRID 1880380 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH3:12].O1CCOCC1.[C:19](=O)([O-:21])[O-:20].[Na+].[Na+]>O>[Cl:11][C:9]1[CH:10]=[C:2]([C:19]([OH:21])=[O:20])[CH:3]=[C:4]2[C:8]=1[NH:7][N:6]=[C:5]2[CH3:12]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 178434328HCID 178434328, compound

Product 1

HCID 178434330HCID 178434330, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
165 °C

Procedure

A microwave tube was charged with 5-bromo-7-chloro-3-methyl-1H-indazole (610 mg, 2.48 mmol), dioxane (5 mL), Hermann's catalyst (119 mg, 0.12 mmol) and a solution of sodium carbonate (790 mg, 7.46 mmol) in water (10 mL). The mixture was stirred for 20 sec, heated at 165° C. for 30 minutes in a microwave reactor at very high absorption setting. The reaction was vented before handling. The mixture was filtered through diatomaceous earth and washed with EtOAc. The filtrate was concentrated, the residue was dissolved in water and acidified to pH ˜3 with conc HCl. The solids were collected by filtration and dried to afford the title compound (420 mg, 82%).

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. washwashed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. dissolutionthe residue was dissolved in water
  5. filtrationThe solids were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-25abe437904645d8b9f962bd8b4940ed
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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