Diisopropylamine → HCID 57722985, compound

HRID 1987020Notes

Reaction equation

C([Li])CCC.C(NC(C)C)(C)C.[C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH3:14].[Br:21][C:22]1[CH:27]=[C:26]([Br:28])[N:25]=[C:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:35])[C:23]=1[CH2:36]Br>C1COCC1.C(O)(=O)C>[Br:21][C:22]1[CH:27]=[C:26]([Br:28])[N:25]=[C:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:35])[C:23]=1[CH2:36][CH2:14][C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

Conditions

Temperature: -70 °C

Procedure

n-Butyllithium in hexanes (1.6 Molar (hereinafter “M”), 3.75 millilitre (hereinafter “ml”), 6.0 millimole (hereinafter “mmol”)) was added to di-isopropylamine (0.84 ml, 6.0 mmol) in dry THF (15 ml) at −10° under nitrogen. After 5 minutes (hereinafter “min”). the solution was cooled to −70° and tert-butyl acetate (0.5 ml, 3.71 mmol) added dropwise. After stirring at −70° C. for 10 min. under nitrogen, 4,6-Dibromo-3-(bromomethyl)-2-(2-chlorophenyl)pyridine (0.405 grams (hereinafter “g”), 0.92 mmol) in dry THF (15 ml) was added, and the mixture stirred at −70° for 2 h. Glacial acetic acid (2 ml) was added, the temperature allowed to rise to 22° and the solution evaporated in vacuo. The residue was purified by column chromatography over silica (50 g) eluting with cyclohexane-ethyl acetate (9:1)-(5:1) to give the product as an oil (0.21 g).

Workup

temperaturethe solution was cooled to −70°
stirringthe mixture stirred at −70° for 2 h
customto rise to 22°
customthe solution evaporated in vacuo
customThe residue was purified by column chromatography over silica (50 g)
washeluting with cyclohexane-ethyl acetate (9:1)-(5:1)

Sources & evidence

ORD record: ord-5b2b41687d0645238f9f883becec5880
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07550480B2

Reaction notes

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