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

HRID 1269925Notes

Reaction equation

[CH3:1][S-:2].[Na+].Br[C:5]1[C:13]([O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[N:8][N:9]2[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1.O>CN(C)C=O>[CH3:1][S:2][C:5]1[C:13]([O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[N:8][N:9]2[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1

Participants

Conditions

Temperature: 70 °C

Procedure

Sodium thiomethoxide (0.0265 g, 0.38 mmol) was added to a solution of 4-bromo-1-tetrahydro-2H-pyran-2-yl-5-(tetrahydro-2H-pyran-2-yloxy)-1H-indazole (0.100 g, 0.26 mmol) in N,N-dimethylformamide (1 ml), and the resulting mixture was heated at 70° C. and stirred for 11 hours. The reaction solution was added to water and extracted three times with toluene/ethyl acetate=1/1, and the extract solution was dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by a silica gel chromatography (hexane/ethyl acetate=10/1) to obtain 4-(methylthio)-1-tetrahydro-2H-pyran-2-yl-5-(tetrahydro-2H-pyran-2-yloxy)-1H-indazole (0.0737 g, 80%).

Workup

extractionextracted three times with toluene/ethyl acetate=1/1
dry with materialthe extract solution was dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off
customthe residue was purified by a silica gel chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record: ord-2cebfd3f81ac4c879f1d99e621253371
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199147B2

Reaction notes

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