Cesium carbonate → (R)-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-(2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropoxy)-6-fluoroquinoline

HRID 876498ノート

反応式

HRID 876498 の反応式
[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([OH:21])[CH:14]=[C:15]([F:20])[CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.CS(O[CH2:27][C:28]([C@@H:31]1[CH2:35][O:34][C:33]([CH3:37])([CH3:36])[O:32]1)([CH3:30])[CH3:29])(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(N(C)C)=O>[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:21][CH2:30][C:28]([C@@H:31]4[CH2:35][O:34][C:33]([CH3:37])([CH3:36])[O:32]4)([CH3:27])[CH3:29])[CH:14]=[C:15]([F:20])[CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 86654366(R)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropyl methanesulfonateHCID 1363378052-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-8-ol

生成物 1

HCID 67234098(R)-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-(2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropoxy)-6-fluoroquinoline収率 134.8%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
85 °C

実験手順

2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-8-ol (0.09 g, 0.34 mmol), (R)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropyl methanesulfonate (0.11 g, 0.45 mmol) and cesium carbonate (0.22 g, 0.69 mmol) were added to 1 to 2 mL of DMA and heated to 85° C. for 4-5 hours. The reaction was concentrated and treated with water and ethyl acetate. The reaction was extracted several times with ethyl acetate. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified on Silica gel using 2% NH4OH in isopropyl acetate and DCM to provide 200 mgs of the desired product (85% pure).

後処理

  1. concentrationThe reaction was concentrated
  2. additiontreated with water and ethyl acetate
  3. extractionThe reaction was extracted several times with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on Silica gel using 2% NH4OH in isopropyl acetate and DCM

出典と根拠

ORDレコード
ord-b4adb603c10a4a6db88ba8f9723a729e
出典データセット
uspto-grants-2015_03
特許番号
US08987251B2

反応ノート

読み込み中…