Acetone → HCID 22291309, compound

HRID 2307970Notes

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.C([Li])CCC.[CH3:30][C:31]([CH3:33])=[O:32]>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:31]([OH:32])([CH3:33])[CH3:30])=[CH:3][C:4]=2[CH3:24])[C:12]=1[CH3:13])[CH2:18][CH3:19])[CH3:17]

Participants

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-butyllithium 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

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

Sources & evidence

ORD record: ord-6a9c42da348040a680b70f91840362aa
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06833378B2

Reaction notes

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