Sodium Carbonate → HCID 86637901, compound

HRID 2389329Notes

Reaction equation

HRID 2389329 reaction equation
Br[C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:18]2[CH:19]=[C:20]([CH:28]=[CH:29][CH:30]=2)[O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])O1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[OH:9][CH2:8][C:6]1[N:7]=[C:2]([C:18]2[CH:19]=[C:20]([CH:28]=[CH:29][CH:30]=2)[O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:3]=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 3517811(6-Bromopyridin-2-yl)methanolHCID 17749919Ethyl [3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]acetate

Product 1

HCID 86637901HCID 86637901, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of (6-bromopyridin-2-yl)methanol (811 mg) in DME (20 mL) was added Pd(PPh3) 4 (453 mg) at ambient temperature under N2 gas atmosphere. After stirring for 20 minutes, ethyl [3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]acetate (1.20 g) and a solution of 2M Na2CO3 aqueous solution (5.88 mL) were added and the mixture was refluxed for 7 hours. The mixture was cooled to ambient temperature and partitioned between EtOAc (40 mL) and water. The organic layer was washed with saturated NaHCO3 aqueous solution, water and then brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=10:1) to give ethyl {3-[6-(hydroxymethyl)pyridin-2-yl]phenoxy}acetate (297 mg) as a colorless oil.

Workup

  1. temperaturethe mixture was refluxed for 7 hours
  2. custompartitioned between EtOAc (40 mL) and water
  3. washThe organic layer was washed with saturated NaHCO3 aqueous solution, water
  4. dry with materialbrine, dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=10:1)

Sources & evidence

ORD record
ord-f8e84e4ec76f42ef96b11402894e017b
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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