Sodium Carbonate → HCID 178438016, compound

HRID 1880403Notes

Reaction equation

HRID 1880403 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[CH2:12][CH3:13].[C:14](=O)([O-:16])[O-:15].[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]>[Cl:11][C:9]1[CH:10]=[C:2]([C:14]([OH:16])=[O:15])[CH:3]=[C:4]2[C:8]=1[NH:7][N:6]=[C:5]2[CH2:12][CH3:13]

Participants

7

Reactant 2

HCID 10340Sodium CarbonateHCID 178438015HCID 178438015, compound

Product 1

HCID 178438016HCID 178438016, compoundYield 86.4%

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

To a microwave tube were added 5-bromo-7-chloro-3-ethyl-1H-indazole (127.0 mg, 0.49 mmol) dissolved in dioxane (1.0 mL). The Hermann's catalyst ((trans-Bis(acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II))) (23.0 mg, 0.024 mmol) and molybdenum hexacarbonyl (64.4 mg, 0.244 mmol) were added followed by a solution of sodium carbonate (156 mg, 1.47 mmol) in water (2.0 mL). Separation occurs within the vessel. The mixture was stirred for 20 seconds and then the mixture was heated to 165° C. for 15 minutes under mircrowave irradiation with the absorption setting at very high. The reaction was stopped and the vessel was vented before handling. The mixture was filtered and washed with EtOAc. The filtrate was concentrated and the residue was re-dissolved with water. The solution was then acidified to pH ˜3. The solid was collected and dried to afford 7-chloro-3-ethyl-1H-indazole-5-carboxylic acid as a solid (95.0 mg, 86.4%).

Workup

  1. customSeparation
  2. filtrationThe mixture was filtered
  3. washwashed with EtOAc
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe residue was re-dissolved with water
  6. customThe solid was collected
  7. customdried

Sources & evidence

ORD record
ord-9764b5f4611f4e95a4a3ddd59dd19145
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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