Dimethylformamide → HCID 21195140, compound

HRID 1067888Notes

Reaction equation

HRID 1067888 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH:11]=[C:10]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[N:9]=2)[CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[CH:35]=[O:36]>O1CCCC1>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[CH:11]=[C:10]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[N:9]=[C:8]([C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH:35]=[O:36])[N:7]=3)[CH:13]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 21195132HCID 21195132, compoundHCID 178418339Butyllithium

Product 1

HCID 21195140HCID 21195140, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 6-bromo-4′-(4-methoxyphenyl)-2,2′:6′,2″-terpyridine (15.1 mmol) in 100 mL of dry THF is added dropwise to a solution of n-butyl lithium (15.5 mmol) in 20 mL of tetrahydrofuran (THF) at −78° C. under N2 over 12 minutes. After 10 minutes the reaction mixture is treated with dimethylformamide (7.5 mL) in THF (15 mL), and quenched after 15 minutes with aqueous 10% HCl. The product is extracted into cold chloroform which is washed with saturated sodium chloride solution, filtered, and the solvent is evaporated. The residue is triturated with CH3CN, filtered, and recrystallized from ethyl acetate to provide the desired compound.

Workup

  1. customquenched after 15 minutes with aqueous 10% HCl
  2. extractionThe product is extracted into cold chloroform which
  3. washis washed with saturated sodium chloride solution
  4. filtrationfiltered
  5. customthe solvent is evaporated
  6. customThe residue is triturated with CH3CN
  7. filtrationfiltered
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f8778f0114d0418da417672fe27c70ef
Source dataset
uspto-grants-2001_06
Patent number
US06248870B1

Reaction notes

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