Water → Methyl 3-({6-[(3-ethylpyridin-2-yl)oxy]-1-methyl-1H-benzimidazol-2-yl}methoxy)benzoate

HRID 1843695Notes

Reaction equation

HRID 1843695 reaction equation
Br[C:2]1[C:3]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([CH2:17][O:18][C:19]4[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=4)[C:22]([O:24][CH3:25])=[O:23])[N:14]([CH3:29])[C:13]=3[CH:30]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:31](B(CC)CC)[CH3:32].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[CH2:31]([C:2]1[C:3]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([CH2:17][O:18][C:19]4[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=4)[C:22]([O:24][CH3:25])=[O:23])[N:14]([CH3:29])[C:13]=3[CH:30]=2)=[N:4][CH:5]=[CH:6][CH:7]=1)[CH3:32]

Participants

7

Reactant 4

HCID 962WaterHCID 7357TriethylboraneHCID 11430Potassium CarbonateHCID 66705741Methyl 3-({6-[(3-bromopyridin-2-yl)oxy]-1-methyl-1H-benzimidazol-2-yl}methoxy)benzoate

Product 1

HCID 66705843Methyl 3-({6-[(3-ethylpyridin-2-yl)oxy]-1-methyl-1H-benzimidazol-2-yl}methoxy)benzoateYield 51.5%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 3-({6-[(3-bromopyridin-2-yl)oxy]-1-methyl-1H-benzimidazol-2-yl}methoxy)benzoate produced in Example (2a) (1.20 g, 2.56 mmol), triethylborane (1.0 M solution in THF, 5.12 mL, 5.12 mmol), a [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium (II)-dichloromethane mixture (0.21 g, 0.26 mmol) and potassium carbonate (0.71 g, 5.12 mmol) in DMF (10 mL) was stirred in a nitrogen atmosphere at 80° C. for two days. After leaving to cool, water (50 mL) was added to the reaction mixture, followed by extraction with ethyl acetate (50 mL). Then, the organic layer was washed with water (100 mL) twice and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by reverse phase column chromatography (acetonitrile/water, 2:1) to obtain the title compound (0.55 g, 51%) as a white solid.

Workup

  1. customAfter leaving
  2. temperatureto cool
  3. extractionfollowed by extraction with ethyl acetate (50 mL)
  4. washThen, the organic layer was washed with water (100 mL) twice
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationAfter concentration under reduced pressure
  7. customthe residue was purified by reverse phase column chromatography (acetonitrile/water, 2:1)

Sources & evidence

ORD record
ord-4c668d4d368643d791f7ecd4a14a4745
Source dataset
uspto-grants-2015_02
Patent number
US08946264B2

Reaction notes

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