Methanol → HCID 86683168, compound

HRID 920950Notes

Reaction equation

HRID 920950 reaction equation
Cl[C:2]1[C:7]2[C:8](=[O:24])[N:9]([CH2:12][CH2:13][C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]=3)[N:10]=[CH:11][C:6]=2[CH:5]=[N:4][CH:3]=1.CO.C(=O)([O-])[O-].[Na+].[Na+].[N:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1>C1(C)C=CC=CC=1.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.CC(=O)OCC.O>[N:33]1[CH:38]=[CH:37][C:36]([C:2]2[C:7]3[C:8](=[O:24])[N:9]([CH2:12][CH2:13][C:14]4[CH:23]=[CH:22][C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[N:15]=4)[N:10]=[CH:11][C:6]=3[CH:5]=[N:4][CH:3]=2)=[CH:35][CH:34]=1

Participants

9

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 86683167HCID 86683167, compound

Product 1

HCID 86683168HCID 86683168, compoundYield 6.8%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

8-chloro-2-(2-(quinolin-2-yl)ethyl)pyrido[4,3-d]pyridazin-1(2H)-one (34 mg, 0.101 mmol) was suspended in 2 mL of toluene and 2 mL of methanol under argon. Then, an aqueous solution of sodium carbonate (16.5 mg, 0.15 mmol, 2 M) was added. To the suspension, pyridin-4-boronic acid (13.79 mg, 0.101 mmol) and then tetrakis(triphenylphosphine)palladium(0) (11.67 mg, 10.10 μmol) were added. The reaction mixture was heated in a CEM microwave at 130° C. for 30 min. Water and EA were added. The organic phase was extracted with water, dried (MgSO4) and evaporated. The residue was purified by chromatography (eluent: DCM/methanol) and then recrystallized from EA/diisopropyl ether (1:1) to give 2.6 mg (yield: 6.79%) of the title compound as off-white solid. LC-MS: m/e 380.1 (M+H)+

Workup

  1. extractionThe organic phase was extracted with water
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by chromatography (eluent: DCM/methanol)
  5. customrecrystallized from EA/diisopropyl ether (1:1)

Sources & evidence

ORD record
ord-78be5b013a694fb18497b90dc5e242cb
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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