Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | 2-Amino-6-(trifluoromethyl)pyridine | HCID 821024 | — |
| Reactant | 4-Amino-6-bromoquinoline | HCID 2756374 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 57519920 | HCID 57519920 | 159.6% |
Reaction Steps
366 mg of bis(trichloromethyl)carbonate (1.234 mmol) were dissolved in 7 ml of DCM and cooled to 0° C. To this mixture the solution of 400 mg of 6-(trifluoromethyl)pyridin-2-amine (2.467 mmol) and 379 μl of triethylamine (5.43 mmol) in 9.7 ml DCM was slowly added over 60 minutes at 0° C., and stirring was continued for an additional 60 minutes at room temperature. 550 mg of 6-bromoquinolin-4-amine (2.467 mmol) and 379 μl of triethylamine (5.43 mmol) were suspended in 9.7 ml and subsequently slowly added to the reaction mixture at RT, which became a clear solution after 45 minutes. After stirring over night the reaction mixture was poured into ice water and stirred for 2 h. The precipitation formed was filtered off and dried in vacuum for 24 h. 810 mg of the desired product were obtained as an off white powder (yield: 80%). The quite pure raw material was used without further purification in the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09090592B2 |
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| Source dataset | uspto-grants-2015_07 |
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| ORD ID | ord-75cbc8e726af4a1ca4d5fc7b3a9538d9 |
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| Source note | uspto-grants-2015_07 |
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