Hydrochloric Acid → HCID 90417433, compound

HRID 1486821Notes

Reaction equation

HRID 1486821 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]([O:10]C)=[O:9])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:20]2[CH2:21][CH2:22][O:23][CH2:24][CH:25]=2)O1.C([O-])([O-])=O.[Cs+].[Cs+].Cl>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>[O:23]1[CH2:22][CH:21]=[C:20]([C:2]2[N:7]=[N:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=2)[CH2:25][CH2:24]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 12379801Methyl 6-chloropyridazine-3-carboxylate

Product 1

HCID 90417433HCID 90417433, compoundYield 79.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 6-chloropyridazine-3-carboxylate (1.00 g, 5.79 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (1.22 g, 5.79 mmol), Pd(PPh3)4 (536 mg, 0.44 mmol) and Cs2CO3 (3.40 g, 10.4 mmol) were suspended in dioxane (8 mL) and water (8 mL) and heated in a microwave reactor at 125° C. for 30 min. 1M aq HCl (10 mL) was added, the precipitate was removed by filtration and the filtrate was concentrated in vacuo. The residue was passed through a silica pad eluting with 30% MeOH in DCM and concentrated in vacuo to give the title compound as a white solid (946 mg, 79.2%). LCMS (ES+): 207.1 [MH]+. HPLC: Rt 3.30 min, 49.9% purity.

Workup

  1. customthe precipitate was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. washeluting with 30% MeOH in DCM
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c3eb75805b934c7dba8ff3f9dd3aa768
Source dataset
uspto-grants-2016_08
Patent number
US09428498B2

Reaction notes

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