Iodoethane → HCID 21912331, compound

HRID 1760682Notes

Reaction equation

HRID 1760682 reaction equation
Br[C:2]1[CH:22]=[C:21]([CH3:23])[C:5]([O:6][C:7]2[C:12]([CH3:13])=[C:11]([NH:14][CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH:10]=[C:9]([CH3:20])[N:8]=2)=[C:4]([CH3:24])[CH:3]=1.[CH2:25]([Li])[CH2:26]CC.C(I)C>C1COCC1>[CH2:25]([C:2]1[CH:22]=[C:21]([CH3:23])[C:5]([O:6][C:7]2[C:12]([CH3:13])=[C:11]([NH:14][CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH:10]=[C:9]([CH3:20])[N:8]=2)=[C:4]([CH3:24])[CH:3]=1)[CH3:26]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 21912379HCID 21912379, compoundHCID 178418339Butyllithium

Product 1

HCID 21912331HCID 21912331, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [2-(4-bromo-2,6-dimethyl-phenoxy)-3,6-dimethyl-pyridin-4-yl]-(1-ethyl-propyl)amine in dry THF was added n-butyllithium at −78° C. After stirring at −782 C. for 10 min, ethyl iodide was added and the resulting mixture was stirred at −78° C. for 30 min, the dry-ice bath was removed. After stirring for 5 min, the mixture was quenched with brine and extracted with ethyl acetate. The organic layer was separated, dried, and concentrated to dryness. The residue was purified through silica gel chromatography to give the title compound. 1H NMR(CDCl3) d 6.89(s,2H). 6.07(s,1H), 3.72(d,1H), 3.34(m,1H), 2.58(q,2H), 2.16(s,3H), 2.12(s,3H), 2.09(s,6H), 1.4-1.7(m,4H), 1.25(t,3H). 0.96(t,6H) ppm.

Workup

  1. stirringthe resulting mixture was stirred at −78° C. for 30 min
  2. customthe dry-ice bath was removed
  3. stirringAfter stirring for 5 min
  4. customthe mixture was quenched with brine
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was separated
  7. customdried
  8. concentrationconcentrated to dryness
  9. customThe residue was purified through silica gel chromatography

Sources & evidence

ORD record
ord-ad4292855aee4b60ae2036d971d4724f
Source dataset
uspto-grants-2005_01
Patent number
US06844351B1

Reaction notes

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