Sodium Carbonate → HCID 178434277, compound

HRID 1880423Notes

Reaction equation

HRID 1880423 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH3:12].[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>[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][N:6]=1

Participants

7

Reactant 2

HCID 10340Sodium CarbonateHCID 178434272HCID 178434272, compound

Product 1

HCID 178434277HCID 178434277, compoundYield 17%

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

Conditions

Temperature
165 °C

Procedure

To a reaction vessel containing a re-purified solution of 5-bromo-3,7-dimethyl-1H-indazole (prepared as described for Acid Preparation 26, 285 mg, 1.27 mmol) in dioxane (1.3 mL) was added hexacarbonylmolybdenum (264 mg, 1.0 mmol), Herrmann's catalyst (93 mg, 0.1 mmol) and a solution of Na2CO3 in water (636 mg in 2 mL water). The suspension was heated in a microwave at 165° C. for 15 minutes (high absorption). The vial was vented, acidified with 1 N HCl (to pH 2). The reaction mixture was filtered through diatomaceous earth, washed with EtOAc and the organic layer was washed with saturated aqueous NaCl (3×). The organic extract was concentrated to yield the title compound as a pink solid (65 mg, 17%).

Workup

  1. custom(high absorption)
  2. filtrationThe reaction mixture was filtered through diatomaceous earth
  3. washwashed with EtOAc
  4. washthe organic layer was washed with saturated aqueous NaCl (3×)
  5. extractionThe organic extract
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-115e5e6d10a84d73ab6e3eb7c1ba4069
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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