Sodium Carbonate → Methyl 3-(6-aminopyridazin-3-yl)benzoate

HRID 1755298Notes

Reaction equation

HRID 1755298 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:17]2[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=2)[C:20]([O:22][CH3:23])=[O:21])O1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH2:8][C:5]1[N:6]=[N:7][C:2]([C:17]2[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=2)[C:20]([O:22][CH3:23])=[O:21])=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 216436-Amino-3-chloropyridazineHCID 27346513-Methoxycarbonylphenylboronic acid pinacol esterHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

Product 1

HCID 86682701Methyl 3-(6-aminopyridazin-3-yl)benzoateYield 84%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 6-chloropyridazin-3-amine (5 g, 38.6 mmol), methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (15.2 g, 58 mmol), Pd2(dba)3 (2.22 g, 3.86 mmol), X-phos (7.35 g, 15.44 mmol) and Na2CO3 (12.3 g, 115.8 mmol) in dioxane (150 mL) and water (15 mL) was heated to 100° C. with stirring for 6 h under N2. The solvent was removed in vacuo and the resulting residue was purified by chromatography (silica gel, 200-300 mesh, CH2Cl2:MeOH=20:1) to give methyl 3-(6-aminopyridazin-3-yl)benzoate (7.4 g, 84%) as a white solid. LC-MS: [M+H]+, 230.1, tR=1.111 min.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resulting residue was purified by chromatography (silica gel, 200-300 mesh, CH2Cl2:MeOH=20:1)

Sources & evidence

ORD record
ord-f99afef265a9433b92ed9768b03dd5d0
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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