Water → 4-propoxy-1-tetrahydro-2H-pyran-2-yl-5-(tetrahydro-2H-pyran-2-yloxy)-1H-indazole

HRID 1269933Notes

Reaction equation

HRID 1269933 reaction equation
[CH2:1](I)[CH2:2][CH3:3].C(=O)([O-])[O-].[Cs+].[Cs+].[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[N:17]1[C:25]2[CH:24]=[CH:23][C:22]([O:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)=[C:21]([OH:33])[C:20]=2[CH:19]=[N:18]1.O>CN(C)C=O>[CH2:1]([O:33][C:21]1[C:22]([O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)=[CH:23][CH:24]=[C:25]2[C:20]=1[CH:19]=[N:18][N:17]2[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:11]1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 336431-IodopropaneHCID 1363517781-tetrahydro-2H-pyran-2-yl-5-(tetrahydro-2H-pyran-2-yloxy)-1H-indazol-4-ol

Product 1

HCID 694345664-propoxy-1-tetrahydro-2H-pyran-2-yl-5-(tetrahydro-2H-pyran-2-yloxy)-1H-indazoleYield 107.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, n-propyl iodide (257 μl, 2.64 mmol) and cesium carbonate (860 mg, 2.64 mmol) were added to a solution of 1-tetrahydro-2H-pyran-2-yl-5-(tetrahydro-2H-pyran-2-yloxy)-1H-indazol-4-ol (700 mg, 2.20 mmol) in N,N-dimethylformamide (7 ml) at room temperature. After 2 hours, the reaction solution was poured into water and extracted with ethyl acetate. The extract solution was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 4-propoxy-1-tetrahydro-2H-pyran-2-yl-5-(tetrahydro-2H-pyran-2-yloxy)-1H-indazole (852.6 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe extract solution was concentrated under reduced pressure
  3. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-449db7c160aa421d845a70a1286779e0
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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