1,2-Dimethoxyethane → 4-(1-Ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenol

HRID 573269Notes

Reaction equation

HRID 573269 reaction equation
Br[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]([CH2:11][CH3:12])[N:3]=1.[OH:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:11]([N:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:2]([C:17]2[CH:18]=[CH:19][C:14]([OH:13])=[CH:15][CH:16]=2)=[N:3]1)[CH3:12]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 667278823-bromo-1-ethyl-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 1363976914-(1-Ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenolYield 36.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Procedure

A mixture of 3-bromo-1-ethyl-1H-pyrazolo[4,3-b]pyridine (904 mg), (4-hydroxyphenyl)boronic acid (690 mg), Pd(PPh3)4 (139 mg), Na2CO3 (1.48 g), DME (17.5 mL), and H2O (3.5 mL) was refluxed overnight under Ar atmosphere. 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 purified by basic silica gel column chromatography (AcOEt) and crystallized from hexane/AcOEt to give the title compound (353 mg).

Workup

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

Sources & evidence

ORD record
ord-14d45c33483b4ed7acec7e821dbddff2
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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