Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | 1-[3-(Aminomethyl)phenyl]-N,N-dimethylmethanamine | HCID 16228070 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | 6-Bromo-4-chlorophthalazin-1(2H)-one | HCID 53308487 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 58447296 | HCID 58447296 | 24.3% |
Reaction Steps
A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (156 mg, 0.601 mmol), 3-dimethylaminomethylbenzylamine (110 mg, 0.67 mmol), Pd2(dba)3 (49 mg, 0.0535 mmol), rac-BINAP (108 mg, 0.173 mmol) and NaOtBu (143 mg, 1.488 mmol) in DMA (5 mL) was heated at 85° C. for 1 h. The mixture was allowed to cool, diluted with EtOAc and washed with water. The organic layer was washed with sat.aq. NaHCO3, brine and dried (Na2SO4). Preparatory HPLC afforded 4-chloro-6-(3-dimethylaminomethyl-benzylamino)-2H-phthalazin-1-one hydroformate (50 mg) as a pale brown solid. 1H (400 MHz, d6-DMSO) δ: 2.21 (s, 6H), 3.46 (s, 2H), 4.51 (d, 2H), 6.90 (s, 1H), 7.25 (m, 2H), 7.36 (m, 2H), 7.40 (s, 1H), 7.77 (t, 1H), 8.02 (s, 1H), 8.27 (s, 1H), 12.42 (s, 1H), ppm; m/z (M+1) 343.05.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08044041B2 |
|---|
| Source dataset | uspto-grants-2011_10 |
|---|
| ORD ID | ord-74bca2ffee7f4b698b9121fd08259faf |
|---|
| Source note | uspto-grants-2011_10 |
|---|
