Tetrahydrofuran → HCID 86584324, compound

HRID 1831670Notes

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.C1C[O:33][CH2:32]C1>>[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]([CH:32]=[O:33])=[CH:3][C:4]=2[CH3:24])[C:12]=1[CH3:13])[CH2:18][CH3:19])[CH3:17]

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 21912379HCID 21912379, compound

HCID 178418339Butyllithium

Product 1

HCID 86584324HCID 86584324, compound

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, n,N-dimethylformamide was added and the resulting mixture was stirred at −78° C. for 20 min, the dry-ice bath was removed. After stirring for 5 min, the mixture was quenched with diluted HCl, water and adjusted to pH7.5 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 9.93(s,1H), 7.60(s,2H), 6.10(s,1H), 3.75(d,1H), 3.35(mlH), 2.17(s,6H), 2.13(s,3H), 2.12(s,3H), 1.4–1.8(m,4H), 0.97(t,6H) ppm.

Workup

stirringthe resulting mixture was stirred at −78° C. for 20 min
customthe dry-ice bath was removed
stirringAfter stirring for 5 min
customthe mixture was quenched with diluted HCl, water
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-2786d62df74e466c82a463fa9c5d138b
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067664B1

Reaction notes

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