1,2-Dimethoxyethane → 1-Ethyl-3-[4-(3H-imidazo[4,5-b]pyridin-2-yloxy)phenyl]-1H-pyrazolo[4,3-b]pyridine

HRID 573294Notes

Reaction equation

HRID 573294 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:32]=[CH:31][C:12]([O:13][C:14]3[N:22](COCC[Si](C)(C)C)[C:17]4=[N:18][CH:19]=[CH:20][CH:21]=[C:16]4[N:15]=3)=[CH:11][CH:10]=2)O1.Br[C:35]1[C:39]2=[N:40][CH:41]=[CH:42][CH:43]=[C:38]2[N:37]([CH2:44][CH3:45])[N:36]=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>[CH2:44]([N:37]1[C:38]2[C:39](=[N:40][CH:41]=[CH:42][CH:43]=2)[C:35]([C:9]2[CH:10]=[CH:11][C:12]([O:13][C:14]3[NH:22][C:17]4=[N:18][CH:19]=[CH:20][CH:21]=[C:16]4[N:15]=3)=[CH:31][CH:32]=2)=[N:36]1)[CH3:45]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 667278823-bromo-1-ethyl-1H-pyrazolo[4,3-b]pyridineHCID 866889692-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-3-{[2-(trimethylsilyl)ethoxy]methyl}-3H-imidazo[4,5-b]pyridine

Product 1

HCID 1784630051-Ethyl-3-[4-(3H-imidazo[4,5-b]pyridin-2-yloxy)phenyl]-1H-pyrazolo[4,3-b]pyridineYield 118%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Procedure

A mixture of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-3-{[2-(trimethylsilyl)ethoxy]methyl}-3H-imidazo[4,5-b]pyridine (100 mg), 3-bromo-1-ethyl-1H-pyrazolo[4,3-b]pyridine (140 mg), Pd(PPh3)4 (7 mg), Na2CO3 (79 mg), DME (5 mL), and water (1 mL) was refluxed overnight under Ar atmosphere. The mixture was poured into water and extracted with AcOEt. The extract was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) and recrystallized from AcOEt/hexane to give the title compound (90 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 Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)
  7. customrecrystallized from AcOEt/hexane

Sources & evidence

ORD record
ord-1f9d26dfb62241e4bf0e2bf9d81ad895
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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