Water → HCID 86688961, compound

HRID 573276Notes

Reaction equation

HRID 573276 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[N:20]([CH2:27][CH3:28])[N:19]=2)=[CH:14][CH:13]=1)=[O:11].CI.[C:31]([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:27]([N:20]1[C:21]2[C:22](=[N:23][CH:24]=[CH:25][CH:26]=2)[C:18]([C:15]2[CH:14]=[CH:13][C:12]([C:10]([C:2]3[N:1]([CH3:31])[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)=[O:11])=[CH:17][CH:16]=2)=[N:19]1)[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66728259HCID 66728259, compound

Product 1

HCID 86688961HCID 86688961, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A suspension of 1H-benzimidazol-2-yl[4-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenyl]methanone (147 mg), MeI (0.037 mL), and K2CO3 (111 mg) in DMF (1.5 ml) was stirred overnight at 40° C. The reaction mixture was poured into water and extracted with AcOEt. The extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/AcOEt) and crystallized from hexane/AcOEt to give the title compound (139 mg).

Workup

  1. extractionextracted with AcOEt
  2. washThe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (hexane/AcOEt)
  6. customcrystallized from hexane/AcOEt

Sources & evidence

ORD record
ord-7e3f512cb837461ea2f38db422d01eeb
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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