Water → HCID 15404605, compound

HRID 1419500Notes

Reaction equation

HRID 1419500 reaction equation
[Li+].CC([N-]C(C)C)C.[O:9]([C:11]1[C:16]([Br:17])=[CH:15][CH:14]=[C:13]([O:18][CH3:19])[N:12]=1)[CH3:10].Cl[P:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>C1COCC1>[CH3:10][O:9][C:11]1[C:16]([Br:17])=[C:15]([P:21]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:14]=[C:13]([O:18][CH3:19])[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 66180ChlorodiphenylphosphineHCID 6428603-bromo-2,6-dimethoxypyridineHCID 2724682Lithium diisopropylamide

Product 1

HCID 15404605HCID 15404605, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a magnetically stirred solution of 4.0 mL of approximatly 2.0M LDA solution (in hexane) (7.98 mmol) was added a solution of 2,6-dimethoxyl-3-bromopyridine (3.14 g, 6.14 mmol) in 10 mL of THF at -78° C. over a period 20 minutes while the internal temperature was kept below -78° C. To the resulting red-brown suspension was added a solution of chlorodiphenylphosphine (1.20 mL, 6.75 mmol) in the 10 mL of THF at -78° C. The reaction mixture was allowed to warm to ambient temperature overnight and was poured into 20 mL water. The organic product was extracted with dichloromethane (3×20 mL). The combined extract was dried with anhydrous magnesium sulfate and was concentrated in vaccuo to give a crude product which was recrystallized in methanol to give 2.34 g of pure product (95% theoretical yield).

Workup

  1. customwas kept below -78° C
  2. extractionThe organic product was extracted with dichloromethane (3×20 mL)
  3. extractionThe combined extract
  4. dry with materialwas dried with anhydrous magnesium sulfate
  5. concentrationwas concentrated in vaccuo
  6. customto give a crude product which
  7. customwas recrystallized in methanol

Sources & evidence

ORD record
ord-b47c98b3e42145c083634eb259cae9b6
Source dataset
uspto-grants-1999_03
Patent number
US05886182

Reaction notes

Loading…