Potassium Carbonate → (S)-1-[6-(1-Methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]ethanol

HRID 912056Notes

Reaction equation

HRID 912056 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C@@H:11]([OH:13])[CH3:12])=[N:9][N:10]=2)[N:7]=1.[CH3:14][N:15]1[CH:19]=[C:18](B2OC(C)(C)C(C)(C)O2)[CH:17]=[N:16]1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>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.O>[CH3:14][N:15]1[CH:19]=[C:18]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([C@@H:11]([OH:13])[CH3:12])=[N:9][N:10]=3)[N:7]=2)[CH:17]=[N:16]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 57812716(S)-1-(6-chloro[1,2,4]triazolo[4,3-b]pyridazin-3-yl)ethanol

Product 1

HCID 57812656(S)-1-[6-(1-Methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]ethanol

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of (S)-1-(6-chloro[1,2,4]triazolo[4,3-b]pyridazin-3-yl)ethanol (30.0 mg, 0.151 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (62.8 mg, 0.302 mmol), Pd(PPh3)4 (20 mg, 0.02 mmol), potassium carbonate (62.6 mg, 0.453 mmol) and 4:1 dioxane:water (5 mL) was heated to 85° C. for 1 h. The organic solvent was removed in vacuo, and the material was transferred to a separatory funnel and extracted with DCM. The organic layer was dry-loaded onto silica gel, and the material was purified via column chromatography, eluting with 10% MeOH/DCM. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. MS (ES+): m/z 245.08 (100) [MH+]. HPLC: tR=2.00 min (ZQ3, polar—5 min).

Workup

  1. customThe organic solvent was removed in vacuo
  2. customthe material was transferred to a separatory funnel
  3. extractionextracted with DCM
  4. customthe material was purified via column chromatography
  5. washeluting with 10% MeOH/DCM
  6. additionThe fractions containing the pure product
  7. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-aa1ec53a9cda47328cc3fe0612a41539
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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