Pyridine → 1-(4-Methoxyphenyl)-4-(phenylmethoxy)-1H-indazole

HRID 2423086ノート

反応式

HRID 2423086 の反応式
[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[N:12][NH:13]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([N:13]2[C:14]3[C:10](=[C:9]([O:8][CH2:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:17]=[CH:16][CH:15]=3)[CH:11]=[N:12]2)=[CH:22][CH:21]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 201262(4-Methoxyphenyl)boronic acidHCID 231344734-(Benzyloxy)-1h-indazole

生成物 1

HCID 592729721-(4-Methoxyphenyl)-4-(phenylmethoxy)-1H-indazole収率 21.1%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

The 4-[(phenylmethyl)oxy]-1H-indazole (D1) (543 mg, 1.65 mmol), the [4-(methyloxy)phenyl]boronic acid (500 mg, 3.29 mmol), copper (II) acetate (448 mg, 2.47 mmol), powdered molecular sieves (400 mg) and pyridine (0.27 mL, 3.29 mmol) in DCM (75 mL) were stirred at room temperature in the presence of air. After 4 hours the mixture was filtered through a pad of celite and washed with water. The aqueous was re-extracted with DCM and the combined organics were washed with brine and dried over MgSO4. The crude (880 mg) was purified by flash chromatography (Biotage SP4) with a gradient of Et2O (0 to 30%) in hexane to afford 115 mg of title compound (D32).

後処理

  1. filtrationAfter 4 hours the mixture was filtered through a pad of celite
  2. washwashed with water
  3. extractionThe aqueous was re-extracted with DCM
  4. washthe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. customThe crude (880 mg) was purified by flash chromatography (Biotage SP4) with a gradient of Et2O (0 to 30%) in hexane

出典と根拠

ORDレコード
ord-a7c699bfc0e04a1790fdddb82485adb7
出典データセット
uspto-grants-2011_06
特許番号
US07960563B2

反応ノート

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