Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzylamine | HCID 7504 | — |
| Reactant | Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane | HCID 11618717 | — |
| Reactant | HCID 58404689 | HCID 58404689 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 58404896 | HCID 58404896 | — |
Reaction Steps
3-bromo-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine (25.0 mg, 0.081 mmol), benzyl amine (12.0 mg, 0.011 mmol), tris[dibenzylideneacetone]dipalladium (0) (1.9 mg, 0.0020 mmol), and tert-butyl X-phos (3.5 mg, 8.1 mmol) were suspended in toluene (1.6 ml), sparged with argon for 3 minutes, then heated to 100° C. After 12 hours, the reaction mixture was concentrated. The residue was purified by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.05% TFA to give N-benzyl-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-amine 1H NMR (500 MHz, DMSO-d6) δ 8.23 (s, 1H); 8.17 (s, 1H); 7.91 (s, 1H); 7.38 (d, 2H); 7.29 (t, 2H); 7.25 (s, 1H); 7.20 (t, 1H); 6.44 (s, 1H); 4.92 (t, 1H); 4.23 (d, 2H); 3.93 (s, 3H); 3.83 (s, 3H). LRMS (ESI) calculated for C19H20N5O [M+H]+, 334.2; found 334.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08455477B2 |
|---|
| Source dataset | uspto-grants-2013_06 |
|---|
| ORD ID | ord-0cbb3556ec924a0bb32032733d0a1074 |
|---|
| Source note | uspto-grants-2013_06 |
|---|
