8-Hydroxyquinoline → HCID 89699972、化合物

HRID 1055649ノート

反応式

HRID 1055649 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:17][C:18]1[NH:19][CH:20]=[CH:21][N:22]=1.OC1C=CC=C2C=1N=CC=C2>CN(C=O)C.C(=O)(O)[O-].C([N+](CC)(CC)CC)C.[Cu]I>[CH3:17][C:18]1[N:19]([C:2]2[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=2)[C:5]([OH:7])=[O:6])[CH:20]=[CH:21][N:22]=1

参加物

7

反応物 3

HCID 19238-HydroxyquinolineHCID 127492-MethylimidazoleHCID 581374213-Bromo-5-(pentafluorosulfur)benzoic acid

生成物 1

HCID 89699972HCID 89699972、化合物

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 11805541Tetraethylammonium bicarbonate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
160 °C

実験手順

1.0 g (3.06 mmol) of the compound of Example 15A and 276 mg (3.36 mmol) of 2-methylimidazole were dissolved in 20 ml of DMF and 2 ml of water, and the mixture was degassed with argon. 2.06 g (6.42 mmol) of tetraethylammonium bicarbonate were added carefully, followed by 232 mg (1.22 mmol) of copper(I) iodide and 177 mg (1.22 mmol) of 8-hydroxyquinoline. The mixture was heated in a microwave oven (Biotage Initiator, with Dynamic Field Tuning) at 160° C. for 60 min. The reaction was then filtered, and the filtrate was adjusted at pH 1 with concentrated hydrochloric acid and concentrated under reduced pressure. The residue was separated into its components by preparative HPLC (Method 17). Evaporation of the product fractions and drying of the residue under high vacuum gave 238 mg (94% pure, 22% of theory) of the title compound.

後処理

  1. custom2 ml of water, and the mixture was degassed with argon
  2. filtrationThe reaction was then filtered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was separated into its components by preparative HPLC (Method 17)
  5. customEvaporation of the product fractions
  6. customdrying of the residue under high vacuum

出典と根拠

ORDレコード
ord-96a6f56361a04f6d845369da31940732
出典データセット
uspto-grants-2016_07
特許番号
US09394309B2

反応ノート

読み込み中…