Triethylamine → Phosphonic acid, (4′-bromo[2,2′-bipyridin]-4-yl)-, diethyl ester

HRID 481755Notes

Reaction equation

HRID 481755 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][N:9]=2)[CH:3]=1.[CH2:15]([O:17][P:18]([O-:22])[O:19][CH2:20][CH3:21])[CH3:16].C(N(CC)CC)C.C(Cl)Cl.CO>CO>[CH2:15]([O:17][P:18]([C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][N:9]=2)[CH:3]=1)(=[O:22])[O:19][CH2:20][CH3:21])[CH3:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 3780918DiethylphosphiteHCID 155699874,4'-Dibromo-2,2'-bipyridineHCID 21226129Dichloromethane methanol

Product 1

HCID 54420157Phosphonic acid, (4′-bromo[2,2′-bipyridin]-4-yl)-, diethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
98 °C

Procedure

2.0 g of 4,4'-dibromo-2,2-bipyridine (6.4 mmol), 0.9g of palladium tetrakistriphenylphosphine (0.8 mmol), 3.14 g of diethylphosphite (23 mmol) and 2.34 g of triethylamine (23 mmol) are measured into an argon filled 50 ml round bottom. flask, equipped with a cold finger (10 cm) and magnetic stirrer. This is heated on a 98° C. oil bath for 3 hours. The reaction is monitored with TLC on silica gel plates, DCM: MeOH (10:1), Rf-Lb=0.73. This is then cooled back to room temperature, and then the solidified mixture is added to 25 mls of methanol, stirred for 10 min. and evaporated to dryness under reduced pressure.

Workup

  1. additionfilled 50 ml round bottom
  2. customflask, equipped with a cold finger (10 cm) and magnetic stirrer
  3. temperatureThis is then cooled back to room temperature
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-86acc29aeb8a4fe7b2c0cda6adf90d5e
Source dataset
uspto-grants-1998_08
Patent number
US05789592

Reaction notes

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