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

HRID 2035635ノート

反応式

HRID 2035635 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c8bb1749aedf4be48df7cbbeebf08ce1
出典データセット
uspto-grants-2013_11
特許番号
US08575145B2

反応ノート

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