Water → HCID 11182227, compound

HRID 1826243Notes

Reaction equation

HRID 1826243 reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:4][CH:3]=1.Cl[P:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>C(OCC)C>[C:23]1([P:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:2]2[N:7]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:4][CH:3]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 66180ChlorodiphenylphosphineHCID 9921361N-(6-Bromopyridin-2-yl)-2,2-dimethylpropanamide

Product 1

HCID 11182227HCID 11182227, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

1.00 g (3.89 mmol) of 6-bromo-2-pivaloylaminopyridine from example 14.2.1 was dissolved in 10 ml of diethyl ether and admixed at 0° C. with 3.64 ml (8.00 mmol) of (iso-C3H7)MgBr (2.2M in Et2O). The suspension was stirred at 0° C. for 18 h and then admixed with 0.7 ml (0.86 g, 3.89 mmol) of chlorodiphenylphosphine. The mixture was allowed to warm to ambient temperature overnight and was then hydrolyzed by adding 10 ml of dist. H2O. The resulting phases were separated and the aqueous phase was extracted twice with 50 ml each time of ethyl acetate. The organic phases were combined and dried over Na2SO4, and the solvent was removed under reduced pressure. The residue was filtered together with dichloromethane through a short silica gel column (2×10 cm) and the solvent was removed under reduced pressure. The resulting oil was crystallized by digesting with petroleum ether/diethyl ether (40/60). The crystals were filtered off and washed with petroleum ether/diethyl ether (40/60). 0.38 g (1.05 mmol, 27.0%) of 6-(diphenylphosphino)-2-pivaloylaminopyridine was obtained as a solid.

Workup

  1. temperatureto warm to ambient temperature overnight
  2. additionby adding 10 ml of dist
  3. customThe resulting phases were separated
  4. extractionthe aqueous phase was extracted twice with 50 ml each time of ethyl acetate
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed under reduced pressure
  7. filtrationThe residue was filtered together with dichloromethane through a short silica gel column (2×10 cm)
  8. customthe solvent was removed under reduced pressure
  9. customThe resulting oil was crystallized
  10. filtrationThe crystals were filtered off
  11. washwashed with petroleum ether/diethyl ether (40/60)

Sources & evidence

ORD record
ord-9e9bf29279814d65b7d779cb73d725ca
Source dataset
uspto-grants-2006_05
Patent number
US07049473B2

Reaction notes

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