Dimethylformamide → HCID 86651666, compound

HRID 337572Notes

Reaction equation

HRID 337572 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.C([Li])CCC.CN([CH:29]=[O:30])C>C1COCC1>[CH3:18][C:17]([Si:14]([CH3:16])([CH3:15])[O:13][CH2:12][C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([CH:29]=[O:30])[CH:3]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 66895771HCID 66895771, compoundHCID 178418339Butyllithium

Product 1

HCID 86651666HCID 86651666, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a THF (0.06 M) solution of 8-bromo-6-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)quinoline (1 eq.) was added at −78° C. n-butyl lithium (2.5 M in hexane, 2.1 eq.) dropwise over a period of 10 min. The resulting yellow solution was stirred at −78° C. for 15 min before DMF (2 eq.) was added dropwise over a period of 10 min. The now red solution was stirred at −78° C. for another 2 h before the reaction mixture was quenched with the addition of sat. aq. NH4Cl. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were then washed with brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→3:7 (v/v) Hex:EtOAc) afforded the title compound as a yellow oil that solidified upon standing.

Workup

  1. additionwas added dropwise over a period of 10 min
  2. customwas quenched with the addition of sat. aq. NH4Cl
  3. customThe aqueous layer was separated
  4. extractionback-extracted with ether
  5. washThe combined organic extracts were then washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo
  9. customPurification of the crude product
  10. customthus obtained by way of flash chromatography (SiO2, Hex→3:7 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-da46dd2ca58b402cbca7ca7d463a4d47
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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