Water → 4-(6-Chloropyridazin-3-yl)aniline

HRID 2374150Notes

Reaction equation

HRID 2374150 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)O1.[Cl:17][C:18]1[N:19]=[N:20][C:21](Cl)=[CH:22][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.[Cl-].[Na+].O.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>[Cl:17][C:18]1[N:19]=[N:20][C:21]([C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=2)=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 673313,6-DichloropyridazineHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 64052544-(6-Chloropyridazin-3-yl)anilineYield 84.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
110 °C

Procedure

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (0.500 g, 2.28 mmol), 3,6-dichloropyridazine (0.340 g, 2.28 mmol), sodium carbonate (0.726 g, 6.85 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.068 g, 0.059 mmol) were mixed in 1,2-dimethoxyethane (11 mL) and water (3.8 mL) under nitrogen. The reaction mixture was heated (110° C.) for 12 h, cooled to RT, diluted with brine, and extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered, and concentrated under vacuum to a crude solid which was dissolved in DCM and extracted into 1N HCl (aq). The DCM layer was discarded, and the aqueous layer was basified with 1N NaOH (aq) and re-extracted with EtOAc. The EtOAc layer was dried (Na2SO4), filtered, and concentrated under vacuum to give the title compound (0.395 g). MS (ESI+) for m/z 206 (M+H)+.

Workup

  1. temperaturecooled to RT
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum to a crude solid which
  6. dissolutionwas dissolved in DCM
  7. extractionextracted into 1N HCl (aq)
  8. extractionre-extracted with EtOAc
  9. dry with materialThe EtOAc layer was dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0b5e920a0ca94eec864537394c547e90
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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