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

HRID 77480Notes

Reaction equation

HRID 77480 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a29caa52d9d24a1a98c3b41fcb7a1a1b
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Reaction notes

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