Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Cyclopropanemethanamine | HCID 75646 | — |
| Reactant | 6-benzyl-4-chloro-1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine | HCID 118159621 | — |
| Catalyst | Ditert-butyl-[3,6-dimethoxy-2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane;methanesulfonate;palladium(2+);2-phenylaniline | HCID 86346478 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | US9777003, Example 228 | HCID 118159597 | — |
Reaction Steps
A suspension of 6-benzyl-4-chloro-1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (20.0 mg, 0.0644 mmol, from Step 7), cyclopropylmethylamine (51 μL, 0.60 mmol, Aldrich), tBuBrettPhos Pd G3 (6.5 mg, 0.0076 mmol, Aldrich) and Cs2CO3 (0.045 g, 0.14 mmol) in N-methylpyrrolidinone (0.3 mL) and water (0.030 g) was degassed and heated at 100° C. for 4.5 h, after which time the reaction mixture was filtered and the product was purified by preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH). Yield: (10.5 mg, 47%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09309246B2 |
|---|
| Source dataset | uspto-grants-2016_04 |
|---|
| ORD ID | ord-03595e32b47143d6b92f0abc266b72d9 |
|---|
| Source note | uspto-grants-2016_04 |
|---|
