Acetone → HCID 22291309, compound

HRID 967998Notes

Reaction equation

HRID 967998 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.[CH3:25][C:26]([CH3:28])=[O:27]>C1COCC1>[CH2:16]([CH:15]([NH:14][C:11]1[CH:10]=[C:9]([CH3:20])[N:8]=[C:7]([O:6][C:5]2[C:21]([CH3:23])=[CH:22][C:2]([C:26]([OH:27])([CH3:28])[CH3:25])=[CH:3][C:4]=2[CH3:24])[C:12]=1[CH3:13])[CH2:18][CH3:19])[CH3:17]

Participants

4

Reactant 2

HCID 180AcetoneHCID 21912379HCID 21912379, compound

Product 1

HCID 22291309HCID 22291309, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

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-butylithium at −78° C. After stirring at −78° C. for 10 min, acetone 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 7.17(s, 2H), 6.08(s, 1H), 3.73(d, 1H), 3.33(m, 1H), 2.19(s, 3H), 2.15(s, 3H), 2.12(s, 6H), 1.4-1.7(m, 4H), 1.26(s, 6H), 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-5e7109dc1846427eb1e23076f2034d09
Source dataset
uspto-grants-2005_10
Patent number
US06956047B1

Reaction notes

Loading…