Sodium Carbonate → 6-Phenylpyridazin-3-amine
Reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.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]>[C:9]1([C:2]2[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 6-chloropyridazin-3-amine (2 g, 15.4 mmol), phenylboronic acid (2.83 g, 23.2 mmol), Pd2(dba)3 (0.89 g, 1.6 mmol), X-phos (2.94 g, 6.2 mmol) and Na2CO3 (4.91 g, 46.3 mmol) in dioxane (50 mL) and water (5 mL) was heated to 100° C. with stirring for 6 h under N2. The solvent was removed in vacuo and the resulting mixture was purified by chromatography (silica gel, 200-300 mesh, CH2Cl2:MeOH=20:1) to give 6-phenylpyridazin-3-amine (2.06 g, 78%) as a white solid. LC-MS: [M+H]+, 172.1, tR=1.04 min.
Workup
- customThe solvent was removed in vacuo
- customthe resulting mixture was purified by chromatography (silica gel, 200-300 mesh, CH2Cl2:MeOH=20:1)
Sources & evidence
- ORD record
- ord-d731929ecbb94247a898a7505ec170e6
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09169259B2
Reaction notes
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