Sodium Carbonate → HCID 59149722, compound

HRID 1675123Notes

Reaction equation

HRID 1675123 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].FC(F)(F)S(O[C:13]1[CH2:14][CH2:15][N:16]([C:19]2[CH:20]=[CH:21][C:22]3[N:23]([C:25]([C:28]([F:31])([F:30])[F:29])=[N:26][N:27]=3)[N:24]=2)[CH2:17][CH:18]=1)(=O)=O.CC1(C)C(C)(C)OB([C:42]2[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=2)O1>COCCOC.O.CCOC(C)=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>[F:29][C:28]([F:31])([F:30])[C:25]1[N:23]2[N:24]=[C:19]([N:16]3[CH2:17][CH:18]=[C:13]([C:42]4[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=4)[CH2:14][CH2:15]3)[CH:20]=[CH:21][C:22]2=[N:27][N:26]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27346563-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 59578372HCID 59578372, compound

Product 1

HCID 59149722HCID 59149722, compoundYield 80.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Sodium carbonate (114 mg, 1.08 mmol) was added to 1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]-1,2,3,6-tetrahydropyridin-4-yl trifluoromethanesulfonate (150 mg, 0.36 mmol) and 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (81 mg, 0.40 mmol) in a mixture of DME (2 mL) and water (0.5 mL). The mixture was bubbled with nitrogen for 10 minutes then tetrakis(triphenylphosphine)palladium(0) (20.77 mg, 0.02 mmol) was added and the mixture was stirred at 80° C. for 3 hours. The reaction mixture was cooled to room temperature and diluted with EtOAc (3 mL) and water (2 mL). The organic layer was separated and dried, and the solvent was evaporated to give crude product. Purification by flash silica chromatography, elution gradient 0 to 3% MeOH in DCM, gave 1′-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]-1′,2′,3′,6′-tetrahydro-3,4′-bipyridine (100 mg, 80%).

Workup

  1. customThe mixture was bubbled with nitrogen for 10 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe organic layer was separated
  4. customdried
  5. customthe solvent was evaporated
  6. customto give crude product
  7. customPurification
  8. washby flash silica chromatography, elution gradient 0 to 3% MeOH in DCM

Sources & evidence

ORD record
ord-a1294d8bec5049ff87a9dc08cd2235cd
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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