Toluene → 1-(tetrahydro-2H-pyran-2-yl)-5-vinyl-1H-indazole

HRID 77480ノート

反応式

HRID 77480 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[N:6]=[CH:5]2.C([O-])([O-])=O.[K+].[K+].[C:23]1(C)C=CC=C[CH:24]=1>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:11]1[N:7]1[C:8]2[C:4](=[CH:3][C:2]([CH:23]=[CH2:24])=[CH:10][CH:9]=2)[CH:5]=[N:6]1

参加物

6

反応物 3

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 534338265-bromo-1-(oxan-2-yl)-1H-indazole

生成物 1

HCID 866797701-(tetrahydro-2H-pyran-2-yl)-5-vinyl-1H-indazole収率 74%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

反応条件

温度
110 °C

実験手順

To a solution of 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (0.5 g, 1.778 mmol) in toluene (10 mL) and water (10 mL) were added K2CO3 (0.492 g, 3.56 mmol), trivinylboroxin pyridine complex (0.514 g, 2.134 mmol), and Tetrakis (0.206 g, 0.178 mmol). The reaction mixture was heated at 110° C. for 4 h. The reaction mixture was concentrated and the residue was extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated to give 1-(tetrahydro-2H-pyran-2-yl)-5-vinyl-1H-indazole (0.3 g, 74%). LCMS (ES-API), m/z 144 (M-THP).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe residue was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-a29caa52d9d24a1a98c3b41fcb7a1a1b
出典データセット
uspto-grants-2014_09
特許番号
US08841301B2

反応ノート

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