Sodium Carbonate → 2-[6-(4-Fluoro-phenyl)-pyridazin-3-yloxy]-(1-piperidin-1-yl)-ethanone

HRID 1931386Notes

Reaction equation

HRID 1931386 reaction equation
Br[C:2]1[N:7]=[N:6][C:5]([O:8][CH2:9][C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1.[F:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[N:7]=[N:6][C:5]([O:8][CH2:9][C:10]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)=[O:11])=[CH:4][CH:3]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 866381212-(6-Bromo-pyridazin-3-yloxy)-(1-piperidin-1-yl)-ethanone

Product 1

HCID 591522632-[6-(4-Fluoro-phenyl)-pyridazin-3-yloxy]-(1-piperidin-1-yl)-ethanone

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

95 mg (0.326 mmol) of 2-(6-bromo-pyridazin-3-yloxy)-(1-piperidin-1-yl)-ethanone, 46.7 mg (0.334 mmol) 4-fluoro-phenylboronic acid, 11 mg (0.01 mmol) of tetrakis(triphenylphosphine)palladium and 0.5 ml of a 1 M aqueous sodium carbonate solution in 15 ml of DME were heated under reflux for 3 h. After cooling, the mixture was poured onto water and extracted with ethyl acetate. The combined organic phases were dried and evaporated, and the product was purified by RP18 chromatography. Yield: 73 mg.

Workup

  1. temperatureunder reflux for 3 h
  2. temperatureAfter cooling
  3. additionthe mixture was poured onto water
  4. extractionextracted with ethyl acetate
  5. customThe combined organic phases were dried
  6. customevaporated
  7. customthe product was purified by RP18 chromatography

Sources & evidence

ORD record
ord-c840eea19cb6420da61baf9cd2efedc0
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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