Diisopropylamine → HCID 86752140, compound

HRID 1421249Notes

Reaction equation

HRID 1421249 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][C:14]([NH:17][C:18]([C:20]1([Br:27])[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][NH:21]1)=[O:19])([CH3:16])[CH3:15].[Cl:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32]Br>C1COCC1>[CH3:16][C:14]([NH:17][C:18]([C:20]1([Br:27])[C:25]([CH2:26][CH2:32][C:31]2[CH:34]=[CH:35][CH:36]=[C:29]([Cl:28])[CH:30]=2)=[CH:24][CH:23]=[CH:22][NH:21]1)=[O:19])([CH3:13])[CH3:15]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 86752141HCID 86752141, compoundHCID 178418339Butyllithium

Product 1

HCID 86752140HCID 86752140, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Cool diisopropylamine dissolved in THF (60 mL) to 0-5° C. Add n-butyl lithium(39 mL, 97.99 mmol.) and stir the reaction at that temperature for 30 min. Canulate this reaction mixture to a cooled solution of N-(1,1-dimethylethyl)-2-bromo-3-methyl pyridine carboxamide (9.91 g, 97.99 mmol) in dry THF (250 mL) (-70° C.). Stir for 0.5 h then add 3-chlorobenzyl bromide(11.4 g, 55.31 mmol) dissolved in 50 mL of THF. Stir the reaction mixture for 0.5 h. Quench the reaction with water and extract the products twice with EtOAc. Dry the organic phase over Na2SO4, filter and chromatograph on silica gel column eluting with 3% MeOH solution in CH2Cl2 to give the title compound (15 g, Yield 60%).

Workup

  1. customthe reaction at that temperature for 30 min
  2. stirringStir the reaction mixture for 0.5 h
  3. customQuench
  4. customthe reaction with water
  5. extractionextract the products twice with EtOAc
  6. dry with materialDry the organic phase over Na2SO4
  7. filtrationfilter
  8. washchromatograph on silica gel column eluting with 3% MeOH solution in CH2Cl2

Sources & evidence

ORD record
ord-da6a714925f84290a6554abcf27cd02f
Source dataset
uspto-grants-2000_06
Patent number
US06075025

Reaction notes

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