1,2-Dimethoxyethane → HCID 58629869, compound

HRID 1391801Notes

Reaction equation

HRID 1391801 reaction equation
C([O-])([O-])=O.[Na+].[Na+].COCCOC.Br[C:14]1[N:19]=[C:18]([C@@H:20]([OH:25])[CH2:21][O:22][CH2:23][CH3:24])[CH:17]=[CH:16][CH:15]=1.[C:26]([C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)#[N:27]>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>[CH2:23]([O:22][CH2:21][C@@H:20]([C:18]1[N:19]=[C:14]([C:31]2[CH:32]=[CH:33][C:28]([C:26]#[N:27])=[CH:29][CH:30]=2)[CH:15]=[CH:16][CH:17]=1)[OH:25])[CH3:24]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 58629842HCID 58629842, compound

Product 1

HCID 58629869HCID 58629869, compoundYield 130%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Pd(PPh3)4 (187 mg, 0.162 mmol) and Na2CO3 (1.29 g, 12.2 mmol) was treated with DME (20 mL) and stirred under nitrogen for 2 min. Water (10 mL), (1R)-1-(6-bromo-2-pyridinyl)-2-(ethyloxy)ethanol (1.0 g, 4.1 mmol) and (4-cyanophenyl)boronic acid (656 mg, 4.47 mmol) were added and the stirred reaction mixture heated at 80° C. for 17 h. The mixture was then allowed to cool to ambient temperature and the residue partitioned between saturated NH4Cl (100 mL) and EtOAc (100 mL). The aqueous phase was extracted with EtOAc (2×100 mL) and the combined organic extracts washed with brine (100 mL), dried (Na2SO4) and evaporated to give a yellow oil (1.43 g). Purification by Biotage™ chromatography (silica, 40 g cartridge) eluting with cyclohexane:EtOAc (4:1) afforded the title compound as a pale yellow oil (945 mg).

Workup

  1. customthe stirred reaction mixture
  2. temperatureto cool to ambient temperature
  3. customthe residue partitioned between saturated NH4Cl (100 mL) and EtOAc (100 mL)
  4. extractionThe aqueous phase was extracted with EtOAc (2×100 mL)
  5. washthe combined organic extracts washed with brine (100 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-b04b11ebb08a47468e3543d5c0befa86
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

Loading…