HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Methylquinoline → (E)-4-(5-Bromo-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-8-yl)morpholine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Methylquinoline | HCID 7060 | — |
| Reactant | Bromotrimethylsilane | HCID 76113 | — |
| Reactant | 5-Bromo-8-morpholinoimidazo[1,2-a]pyrazine-2-carbaldehyde | HCID 117728113 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (E)-4-(5-Bromo-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-8-yl)morpholine | HCID 117728505 | 93.3% |
Reaction Steps
To a solution of compound 2a (800 mg, 2.58 mmol) in DMF (10 mL) was added 2-methylquinoline (600 mg, 4.20 mmol) and bromotrimethylsilane (960 mg, 8.89 mmol). The reaction mixture was stirred in a 20 mL sealed tube at 90° C. for 4 h. After cooling to rt, the reaction was quenched with MeOH (20 mL). The solids were collected by filtration and washed with Et2O to obtain compound 2b as a red solid (1.05 g, 85% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C21H18BrN5O: 436.1 (M+H). found: 436.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09249163B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-d0ae6533bf0f44439cb6e447ce92593d |
| Source note | uspto-grants-2016_02 |