1,2-Dimethoxyethane → HCID 178489263, compound

HRID 2037184Notes

Reaction equation

HRID 2037184 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH3:23])[C:14]3[C:13]([C:24]([CH2:27][OH:28])([CH3:26])[CH3:25])=[N:12][NH:11][C:10]=3[C:9]2=[O:29])=[CH:4][CH:3]=1.[S:30]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].COCCOC>O>[OH:28][CH2:27][C:24]([C:13]1[C:14]2[CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH3:23])[N:8]([C:5]3[CH:4]=[CH:3][C:2]([C:32]4[CH:33]=[CH:34][S:30][CH:31]=4)=[CH:7][CH:6]=3)[C:9](=[O:29])[C:10]=2[NH:11][N:12]=1)([CH3:25])[CH3:26]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 62657Potassium Phosphate, TribasicHCID 581760Thiophene-3-boronic acidHCID 1784892625-(4-bromophenyl)-3-(1-hydroxymethyl-1-methylethyl)-4-(2-methoxyphenyl)-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazole-6-one

Product 1

HCID 178489263HCID 178489263, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-(4-bromophenyl)-3-(1-hydroxymethyl-1-methylethyl)-4-(2-methoxyphenyl)-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazole-6-one (0.15 g, 0.33 mmol), thiophene-3-yl boronic acid (0.063. g, 0.49 mmol), tripotassium phosphate (0.21 mg, 0.99 mmol), 1,2-Dimethoxyethane (3 mL) and water (0.6 mL) was placed in a flask under nitrogen. To the mixture was added 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (0.027 mg, 0.033 mmol) and the resulting mixture was heated at reflux for 5 hours. After the reaction was completed, the reaction mixture was purified on a silica gel column chromatography (ethyl acetate/n-hexane). The resulting aimed compound was triturated with ethyl acetate and n-hexane to give 3-(1-hydroxymethyl-1-methylethyl)-4-(2-methoxyphenyl)-5-(4-thiophene-3-ylphenyl)-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazole-6-one (0.038 g, yield: 25%) as colorless solid.

Workup

  1. customwas placed in a flask under nitrogen
  2. additionTo the mixture was added 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (0.027 mg, 0.033 mmol)
  3. temperaturethe resulting mixture was heated
  4. temperatureat reflux for 5 hours
  5. customthe reaction mixture was purified on a silica gel column chromatography (ethyl acetate/n-hexane)
  6. customThe resulting aimed compound was triturated with ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-e275393a712a473fbe5b1bfd0faeeade
Source dataset
uspto-grants-2013_11
Patent number
US08575197B2

Reaction notes

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