Cesium carbonate → 4-Iodo-1-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)-1H-pyrazole

HRID 1778724Notes

Reaction equation

HRID 1778724 reaction equation
Br[CH2:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1.[I:11][C:12]1[CH:13]=[N:14][NH:15][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[I:11][C:12]1[CH:13]=[N:14][N:15]([CH2:2][CH2:3][O:4][CH:5]2[CH2:10][CH2:9][CH2:8][CH2:7][O:6]2)[CH:16]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 770224-IodopyrazoleHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyran

Product 1

HCID 593418524-Iodo-1-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)-1H-pyrazoleYield 28.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

At r.t. to a solution of 2-(2-bromoethoxy)tetrahydro-2H-pyran (210 μL, 1.4 mmol) (Aldrich Cat. No. 475394) in acetonitrile (6 mL) was added 4-iodo-1H-pyrazole (0.25 g, 1.3 mmol) (Aldrich Cat. No. 213993), followed by cesium carbonate (0.63 g, 1.9 mmol). The mixture was stirred at r.t. over a weekend. The solid was filtered off, then washed with acetonitrile. The filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.12 g). LCMS (M-84)+=239.0.

Workup

  1. customAt r.t.
  2. filtrationThe solid was filtered off
  3. washwashed with acetonitrile
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)

Sources & evidence

ORD record
ord-4fbfdbfcb66246348e845cac844b7bef
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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