Cesium carbonate → 2-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-6,8-difluoroquinoline

HRID 876472노트

반응식

HRID 876472 반응식
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([F:13])[CH:6]=[C:7]([F:12])[CH:8]=2)[N:3]=1.[N:14]1[N:15]=[CH:16][N:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=12.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:14]1[N:15]=[C:16]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[C:5]([F:13])[CH:6]=[C:7]([F:12])[CH:8]=3)[N:3]=2)[N:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=12

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 249770[1,2,4]Triazolo[4,3-a]pyridineHCID 642093072-Chloro-6,8-difluoroquinoline

생성물 1

HCID 672304752-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-6,8-difluoroquinoline수율 59.5%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

2-Chloro-6,8-difluoroquinoline (0.025 g, 0.125 mmol) was combined with [1,2,4]triazolo[4,3-a]pyridine (0.016 g, 0.14 mmol), micronized Cs2CO3 (0.082 g, 0.25 mmol), and PdCl2(PPh3)2 (0.0088 g, 0.013 mmol), and the solids were slurried in dioxane (1.25 mL). The reaction was degassed with argon (bubbled through the solution) then heated to reflux for 20 hours. The crude reaction mixture was chromatographed without workup on SiO2 eluting with a gradient of 6% NH4OH in MeOH/ethyl acetate to provide the desired product as an orange solid (21 mg).

후처리

  1. customThe reaction was degassed with argon (
  2. custombubbled through the solution)
  3. temperaturethen heated
  4. temperatureto reflux for 20 hours
  5. customThe crude reaction mixture
  6. customwas chromatographed without workup on SiO2 eluting with a gradient of 6% NH4OH in MeOH/ethyl acetate

출처 및 근거

ORD 기록
ord-7794335bce9347b0bdf0fb3bfe10d4ab
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987251B2

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