Water → HCID 68295306, compound

HRID 1501677Notes

Reaction equation

HRID 1501677 reaction equation
[CH:1]1([N:6]2[C:14]3[CH:13]=[C:12]([C:15]4[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=4)[CH:11]=[C:10]([C:22]([O:24][CH3:25])=[O:23])[C:9]=3[CH:8]=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:27][CH2:28][CH2:29][OH:30].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH:1]1([N:6]2[C:14]3[CH:13]=[C:12]([C:15]4[CH:20]=[CH:19][C:18]([O:21][CH2:27][CH2:28][CH2:29][OH:30])=[CH:17][CH:16]=4)[CH:11]=[C:10]([C:22]([O:24][CH3:25])=[O:23])[C:9]=3[CH:8]=[N:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 136344377methyl 1-cyclopentyl-6-(4-hydroxyphenyl)-1H-indazole-4-carboxylate

Product 1

HCID 68295306HCID 68295306, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of methyl 1-cyclopentyl-6-(4-hydroxyphenyl)-1H-indazole-4-carboxylate (0.5 g, 1.48 mmol) in DMF (15 mL), 3-bromopropane-1-ol (0.616 g, 4.46 mmol) and K2CO3 (0.306 g, 2.23 mmol) were added, resulting reaction mass was heated at 100° C. for 4 h. On completion, water was added to reaction mass and extracted with ethyl acetate. Combined organic layers were dried and concentrated under reduced pressure giving crude material which was purified by column chromatography over silica gel (60-120 mesh size) to afford methyl 1-cyclopentyl-6-(4-(3-hydroxypropoxyl)phenyl)-1H-indazole-4-carboxylate (0.4 g, 68.2%).

Workup

  1. customresulting
  2. customreaction mass
  3. extractionextracted with ethyl acetate
  4. customCombined organic layers were dried
  5. concentrationconcentrated under reduced pressure
  6. customgiving crude material which
  7. customwas purified by column chromatography over silica gel (60-120 mesh size)

Sources & evidence

ORD record
ord-7e92387d20bc48b59a72c99ab7447960
Source dataset
uspto-grants-2015_12
Patent number
US09206157B2

Reaction notes

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