Sodium Carbonate → 3-Chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazine

HRID 1661812Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[CH3:9][N:10]1[CH:14]=[C:13](B2OC(C)(C)C(C)(C)O2)[CH:12]=[N:11]1.C([O-])([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[K+].[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOC(C)=O.O1CCOCC1>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:13]2[CH:12]=[N:11][N:10]([CH3:9])[CH:14]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A flask was charged with 3,6-dichloropyridazine (Aldrich, 23.91 g, 160.5 mmol), 1-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (20 g, 96 mmol), 2.0 M Na2CO3 (96 mL) and dioxane (65 mL). Nitrogen was bubbled through the reaction for 60 seconds followed by the addition of Dichlorobis(triphenylphosphine)palladium (0) (6.75 g, 9.6 mmol). The reaction was heated to 80° C. overnight followed by aqueous work up using AcOEt and a solution of K2CO3. After filtration over celite, the organic layer was dried (MgSO4) and concentrated in vacuo. A first fraction of compound (10.2 g) was obtained by crystallization in the solvent (dichoromethane). The filtrate was purified by column chromatography (CH2Cl2 100% and CH2Cl2/MeOH:95/5). The two fractions were gathered and washed with diisopropylether to give the title compound as a yellow solid (12.7 g, 68%).

Workup

customNitrogen was bubbled through the reaction for 60 seconds
filtrationAfter filtration over celite
dry with materialthe organic layer was dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-806f7e4b8e5345ba9133d61c37405e53
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030305B2

Reaction notes

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