3,4-dihydro-2H-pyran → 3-[2-(2-bromophenyl)vinyl]-1-(tetrahydropyran-2-yl)-1H-indazole

HRID 1821358Notes

Reaction equation

HRID 1821358 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][N:11]=1.[O:19]1[CH:24]=[CH:23][CH2:22][CH2:21][CH2:20]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][O:19]2)[N:11]=1

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 69000164(E)-3-[2-(2-bromophenyl)vinyl]-1H-indazole

Product 1

HCID 689987013-[2-(2-bromophenyl)vinyl]-1-(tetrahydropyran-2-yl)-1H-indazoleYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (E)-3-[2-(2-bromophenyl)vinyl]-1H-indazole (0.35 g, 1.2 mmol) obtained in Step 1 of Example 133, 3,4-dihydro-2H-pyrane (0.21 mL, 2.3 mmol) and p-toluenesulfonic acid monohydrate (22 mg, 0.12 mmol) in THF was stirred at 80° C. for 8 hours. After cooling to room temperature, the reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution and extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was reslurried with diisopropylether to obtain 3-[2-(2-bromophenyl)vinyl]-1-(tetrahydropyran-2-yl)-1H-indazole (0.39 g, 86%).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-85b631e3faca4266916704f6a7ece4eb
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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