Sodium Bicarbonate → 2-{4-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-2-methylphenoxy}ethanol

HRID 734790Notes

Reaction equation

HRID 734790 reaction equation
C(=O)(O)[O-].[Na+].Br[C:7]1[CH:8]=[CH:9][C:10]([C:13]#[C:14][C:15]2[CH:24]=[CH:23][C:18]([O:19][CH2:20][CH2:21][OH:22])=[C:17]([CH3:25])[CH:16]=2)=[N:11][CH:12]=1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30](OB(O)O)=[CH:29][CH:28]=1>O1CCOCC1>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([C:7]2[CH:8]=[CH:9][C:10]([C:13]#[C:14][C:15]3[CH:24]=[CH:23][C:18]([O:19][CH2:20][CH2:21][OH:22])=[C:17]([CH3:25])[CH:16]=3)=[N:11][CH:12]=2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 17810664p-Chlorophenylboric acid2×HCID 690586072-[4-(5-Bromopyridin-2-ylethynyl)-2-methylphenoxy]ethanol

Product 1

HCID 673624362-{4-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-2-methylphenoxy}ethanol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

40 mL of 2 N aqueous sodium bicarbonate solution was added to a suspension of 13.20 g (39.74 mmol) of 2-[4-(5-bromopyridin-2-ylethynyl)-2-methylphenoxy]ethanol, 9.32 g (59.60 mmol) of 4-chlorophenylboric acid, and 2.30 g (1.99 mmol) of tetrakis(triphenylphosphane)palladium in 400 mL of 1,4-dioxane and the mixture was refluxed for 12 hours. Another 4.66 g of 4-chlorophenylboric acid and 1.14 g of tetrakis(triphenylphosphane)palladium were added and the mixture was refluxed for 8 hours. The reaction mixture was evaporated down in vacuo and the residue was stirred with EtOAc and water. The precipitate was filtered off, washed with diethyl ether, and dried in vacuo. Yield: 10.70 g (74% of theoretical); C22H18ClNO2 (M=363.837); calc.: molpeak (M+H)+: 364/366 (Cl); found: molpeak (M+H)+: 364/366 (Cl); Rf value: 0.47 (silica gel, DCM/EtOAc 2:1).

Workup

  1. temperaturethe mixture was refluxed for 12 hours
  2. temperaturethe mixture was refluxed for 8 hours
  3. customThe reaction mixture was evaporated down in vacuo
  4. filtrationThe precipitate was filtered off
  5. washwashed with diethyl ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-71883cc4b6dc4e3096aaa7a0c013533f
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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