Glycol monoethyl ether → 1,1,1-Trifluoro-2-[2-(1-phenyl-[1,2,4]triazolo[4,3-a]quinolin-7-ylsulfanyl)-thiazol-5-yl]-butan-2-ol

HRID 2075720ノート

反応式

HRID 2075720 の反応式
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:13][N:14]=[C:7]1[CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].C(O[C:30](=O)[CH2:31][C:32]([OH:43])([C:37]1[S:41][C:40]([SH:42])=[N:39][CH:38]=1)[C:33]([F:36])([F:35])[F:34])C.CCOCCO>CC(O)C.CCOC(C)=O.O.[Cu](I)I>[F:36][C:33]([F:34])([F:35])[C:32]([C:37]1[S:41][C:40]([S:42][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]2[C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[N:13][N:14]=[C:7]2[CH:6]=[CH:5]3)=[N:39][CH:38]=1)([OH:43])[CH2:31][CH3:30]

参加物

9

反応物 4

HCID 8076Glycol monoethyl etherHCID 11430Potassium CarbonateHCID 582577587-Iodo-1-phenyl-[1,2,4]triazolo[4,3-a]quinolineHCID 178472193HCID 178472193、化合物

生成物 1

HCID 670908671,1,1-Trifluoro-2-[2-(1-phenyl-[1,2,4]triazolo[4,3-a]quinolin-7-ylsulfanyl)-thiazol-5-yl]-butan-2-ol

試薬・触媒・溶媒 4

HCID 83717Copper iodide触媒HCID 962Water溶媒HCID 3776Isopropanol溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

7-Iodo-1-phenyl-[1,2,4]triazolo[4,3-a]quinoline (10c, 140 mg, 0.38 mmol), copper iodide (14 mg, 0.08 mmol), and potassium carbonate (105 mg, 0.76 mmol) were suspended in iPrOH (1 mL). 10b (92 mg, 0.38 mmol) in iPrOH (1 mL) was added, followed by ethyl glycol (0.04 mL, 0.76 mmol), and the reaction was heated to 90° C. overnight. The reaction was diluted with EtOAc and water, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (5% MeOH in CH2Cl2), and the isolated product was precipitated from CH2Cl2 to give the desired product, 10d.

後処理

  1. extractionthe aqueous layer was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (5% MeOH in CH2Cl2)
  6. customthe isolated product was precipitated from CH2Cl2

出典と根拠

ORDレコード
ord-b99293a7aa1346f4922e1fa8c3d16d6e
出典データセット
uspto-grants-2011_04
特許番号
US07919621B2

反応ノート

読み込み中…