Sodium Carbonate → Ethyl {2-[4-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenoxy]-1H-benzimidazol-1-yl}acetate

HRID 573318Notes

Reaction equation

HRID 573318 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:30]=[CH:29][C:12]([O:13][C:14]3[N:18]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:17]4[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=4[N:15]=3)=[CH:11][CH:10]=2)O1.Br[C:33]1[C:37]2=[N:38][CH:39]=[CH:40][CH:41]=[C:36]2[N:35]([CH2:42][CH3:43])[N:34]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.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>[CH2:42]([N:35]1[C:36]2[C:37](=[N:38][CH:39]=[CH:40][CH:41]=2)[C:33]([C:9]2[CH:30]=[CH:29][C:12]([O:13][C:14]3[N:18]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:17]4[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=4[N:15]=3)=[CH:11][CH:10]=2)=[N:34]1)[CH3:43]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 667278823-bromo-1-ethyl-1H-pyrazolo[4,3-b]pyridineHCID 86688977Ethyl {2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-1H-benzimidazol-1-yl}acetate

Product 1

HCID 66727897Ethyl {2-[4-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenoxy]-1H-benzimidazol-1-yl}acetateYield 18.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of ethyl {2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-1H-benzimidazol-1-yl}acetate (540 mg), 3-bromo-1-ethyl-1H-pyrazolo[4,3-b]pyridine (289 mg), Pd(PPh3)4 (44.3 mg), Na2CO3 (474 mg) in DME (10 mL) and water (2 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 Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (105 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)

Sources & evidence

ORD record
ord-9639a029461e40bd82144da974fdc9ab
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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