Sodium Carbonate → HCID 66920487, compound

HRID 1880399Notes

Reaction equation

HRID 1880399 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH3:12].O1CCOCC1.[C:19](=O)([O-:21])[O-:20].[Na+].[Na+]>O>[CH3:12][C:5]1[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=[C:2]([C:19]([OH:21])=[O:20])[CH:3]=2)[NH:7][CH:6]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 58639132HCID 58639132, compound

Product 1

HCID 66920487HCID 66920487, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
165 °C

Procedure

A microwave tube was charged with 5-bromo-3,7-dimethyl-1H-indole (317 mg, 1.42 mmol), dioxane (3 mL), Hermann's catalyst (42.1 mg, 0.07 mmol) and a solution of sodium carbonate (450 mg, 4.24 mmol) in water (6 mL). The mixture was stirred for 20 sec, heated at 165° C. for 15 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 and the residue was dissolved in water. The solution was acidified to pH 3 and the solid was collected to afford the title compound (250 mg, 93%).

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. customthe solid was collected

Sources & evidence

ORD record
ord-cadac49f95eb4808abba456b9a1bfffb
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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