Sodium Carbonate → 7-ethyl-1H-indazole-5-carboxylic acid

HRID 1880420Notes

Reaction equation

HRID 1880420 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][CH3:12])[CH:10]=1)[NH:7][N:6]=[CH:5]2.[C:13](=O)([O-:15])[O-:14].[Na+].[Na+]>O1CCOCC1.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].O.C(=[Mo](=C=O)(=C=O)(=C=O)(=C=O)=C=O)=O>[CH2:11]([C:9]1[CH:10]=[C:2]([C:13]([OH:15])=[O:14])[CH:3]=[C:4]2[C:8]=1[NH:7][N:6]=[CH:5]2)[CH3:12]

Participants

7

Reactant 2

HCID 10340Sodium CarbonateHCID 211021955-bromo-7-ethyl-1H-indazole

Product 1

HCID 552714657-ethyl-1H-indazole-5-carboxylic acidYield 74%

Reagents, catalysts & solvents 4

HCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)CatalystHCID 178521658HCID 178521658, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-bromo-7-ethyl-1H-indazole (225 mg, 1.00 mmol) in dioxane (1.5 mL), hexacarbonylmolybdenum (132 mg, 0.50 mmol), Herrmann's catalyst (trans-Bis(acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium) (46.9 mg, 0.05 mmol) and a solution of sodium carbonate (318 mg, 3.00 mmol) in water (2 mL). The suspension was sealed and irradiated in a microwave at 165° C. for 15 minutes (high absorption setting). The vial was vented, filtered through diatomaceous earth, washed with EtOAc and concentrated to provide the title compound (140 mg, 74%).

Workup

  1. customThe suspension was sealed
  2. customirradiated in a microwave at 165° C. for 15 minutes (high absorption setting)
  3. filtrationfiltered through diatomaceous earth
  4. washwashed with EtOAc
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-daa8a384edb4485a8b7c9c5b7a21c4a2
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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