Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | 6-Chloro-3-(3-chlorophenyl)imidazo[1,2-b]pyridazine | HCID 57418686 | — |
| Reactant | sodium 2-methylpropan-2-olate | HCID 178418730 | — |
| Reactant | HCID 178511674 | HCID 178511674 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 178511600 | HCID 178511600 | 37.1% |
Reaction Steps
To a mixture of 6-chloro-3-(3-chlorophenyl)imidazo[1,2-b]pyridazine (500 mg, 1.89 mmol) in toluene (10 mL) was added trans-cyclohexane-1,4-diamine (215.9 mg, 1.89 mmol), t-BuONa (302.4 mg, 3.78 mmol), BINAP (117.7 mg, 0.189 mmol), Pd2(dba)3 (173 mg, 0.189 mmol). The mixture was filled with N2 and heated at 110° C. for 4 h. TLC (PE:EA=1:1) showed the reaction was complete. The reaction was poured into water (150 mL), extracted with EA (3×50 mL). The organic layer was dried and condensed. The residue was purified by combi flash (CH2Cl2:MeOH=0˜10:1) to give trans-N1-(3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)cyclohexane-1,4-diamine (240 mg, yield: 37%) as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09416132B2 |
|---|
| Source dataset | uspto-grants-2016_08 |
|---|
| ORD ID | ord-916c503e66ab4d25baf4201a100cc90d |
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| Source note | uspto-grants-2016_08 |
|---|
