Sodium Carbonate → HCID 66920487, compound

HRID 1880427Notes

Reaction equation

HRID 1880427 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].[C:13](=O)([O-:15])[O-:14].[Na+].[Na+]>O1CCOCC1.O.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[CH3:12][C:5]1[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=[C:2]([C:13]([OH:15])=[O:14])[CH:3]=2)[NH:7][CH:6]=1

Participants

7

Reactant 2

HCID 10340Sodium CarbonateHCID 58639132HCID 58639132, compound

Product 1

HCID 66920487HCID 66920487, compoundYield 93.4%

Reagents, catalysts & solvents 4

HCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
165 °C

Procedure

A 25 mL microwave reaction tube was charged with 317 mg 5-bromo-3,7-dimethyl-1H-indole dissolved in 3 L dioxane. 42 mg trans-Bis(acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) and 187 mg molybdenum hexacarbonyl were added followed by 450 mg sodium carbonate dissolved in 6 mL water. The vial was sealed and heated in a microwave reactor for 20 minutes at 165° C. The reaction was cooled and then filtered through celite, and the filtercake washed with EtOAc. The filtrate was concentrated and the resultant oil was redissolved with water. The solution was acidified to pH 3 and the precipitate collected by filtration to yield 250.0 mg (93%) of 3,7-dimethylindole-5-carboxylic acid. LC-MS @ 188.1 (M−1)

Workup

  1. customThe vial was sealed
  2. temperatureThe reaction was cooled
  3. filtrationfiltered through celite
  4. washthe filtercake washed with EtOAc
  5. concentrationThe filtrate was concentrated
  6. dissolutionthe resultant oil was redissolved with water
  7. filtrationthe precipitate collected by filtration

Sources & evidence

ORD record
ord-cc4ce284be944a4a8ac2443b12737479
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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