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

HRID 77480노트

반응식

HRID 77480 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

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온도
110 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a29caa52d9d24a1a98c3b41fcb7a1a1b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841301B2

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