Water → HCID 68309714, compound

HRID 922447Notes

Reaction equation

HRID 922447 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:12](=[O:14])[CH3:13])=[CH:8][C:9]=2[Cl:11])[N:4]([CH2:15][CH2:16][CH2:17][O:18][CH3:19])[N:3]=1.[C:20](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1.O>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:11][C:9]1[CH:8]=[C:7]([C:12](=[O:14])[CH3:13])[CH:6]=[C:5]2[C:10]=1[C:2]([CH3:20])=[N:3][N:4]2[CH2:15][CH2:16][CH2:17][O:18][CH3:19]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 68309707HCID 68309707, compound

Product 1

HCID 68309714HCID 68309714, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-[3-bromo-4-chloro-1-(3-methoxypropyl)-1H-indazol-6-yl]ethanone (1.0 g) in 1,4-dioxane (20 mL) were added potassium carbonate (1.2 g), trimethylboroxine (0.41 mL) and 1,1′-bis(diphenylphosphino)ferrocene dichloropalladium (II) (212 mg) under argon, and the mixture was heated to stir at 80° C. for 24 hours. Then, thereto was added water under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1→3/2) to give 1-[4-chloro-1-(3-methoxypropyl)-3-methyl-1H-indazol-6-yl]ethanone [REx(15-1)] (392 mg) as a pale yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1→3/2)

Sources & evidence

ORD record
ord-6737f136422b476fae42526e79f2fe77
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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