3,6-Dichloropyridazine → HCID 58300174, compound

HRID 1674991Notes

Reaction equation

HRID 1674991 reaction equation
C([O-])(O)=O.[Na+].[Cl:6][C:7]1[N:8]=[N:9][C:10](Cl)=[CH:11][CH:12]=1.CC1(C)C(C)(C)OB([C:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH:23]=2)O1>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>[Cl:6][C:7]1[N:8]=[N:9][C:10]([C:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH:23]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 673313,6-DichloropyridazineHCID 516892Sodium BicarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 58300174HCID 58300174, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Saturated aqueous NaHCO3 solution (10 mL) was added to a stirred solution of 3,6-dichloropyridazine (0.968 g, 6.5 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (2.010 g, 6.50 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.376 g, 0.33 mmol) in DME (20 mL). The vessel was flushed with nitrogen and the initial suspension was heated at 80° C. for 9 hours. The reaction mixture was diluted with DCM and washed with water. The organic phase was dried over MgSO4 and evaporated. The crude product was purified by MPLC silica chromatography, elution gradient 35 to 45% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford tert-butyl 4-(6-chloropyridazin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.929 g, 48.3%) as a colourless crystalline solid.

Workup

  1. customThe vessel was flushed with nitrogen
  2. additionThe reaction mixture was diluted with DCM
  3. washwashed with water
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated
  6. customThe crude product was purified by MPLC silica chromatography, elution gradient 35 to 45% EtOAc in isohexane
  7. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-a889dd7059534cdf9d065a14dfb0355f
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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