Dimethylformamide → HCID 86635914, compound

HRID 561796Notes

Reaction equation

HRID 561796 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.C([Li])CCC.CN([CH:27]=[O:28])C>C1COCC1>[N:16]1[CH:17]=[CH:18][C:13]([CH2:12][C:4]2[CH:5]=[C:6]3[C:11](=[C:2]([CH:27]=[O:28])[CH:3]=2)[N:10]=[CH:9][CH:8]=[CH:7]3)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 21865546HCID 21865546, compoundHCID 178418339Butyllithium

Product 1

HCID 86635914HCID 86635914, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-bromo-6-(pyridine-4-ylmethyl)quinoline (1 eq.) in THF (0.13 M) was added, at −78° C., n-butyl lithium (2.5 M hexane solution, 1.1 eq) dropwise over 15 min. The reaction mixture was stirred at −78° C. for a further 30 min before DMF (1.5 eq.) was slowly added. The resulting solution was allowed to warm to RT over 3 h and then quenched with H2O. The organic layer was separated and the aqueous layer was back-extracted with EtOAc. The combined organic extracts were washed with sat. aq. NaHCO3 and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded a brown oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 7:3 (v/v) Hex:EtOAc→EtOAc) afforded the title compound.

Workup

  1. additionwas slowly added
  2. customquenched with H2O
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was back-extracted with EtOAc
  5. washThe combined organic extracts were washed with sat. aq. NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customConcentration of the filtrate in vacuo afforded a brown oil
  9. customPurification of the crude product
  10. customthus obtained by way of flash chromatography (SiO2, 7:3 (v/v) Hex:EtOAc→EtOAc)

Sources & evidence

ORD record
ord-e7b1b6d545d14dbeb41baf491fde0fcc
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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