Dimethylformamide → 2-Formyl-1-methyl-4-phenyl-5-[4-pyridyl]imidazole

HRID 479776노트

반응식

HRID 479776 반응식
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:4]=[CH:3]1.C([Li])CCC.CN([CH:27]=[O:28])C>C1COCC1>[CH:27]([C:3]1[N:2]([CH3:1])[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[C:5]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:4]=1)=[O:28]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 187714831-Methyl-4-phenyl-5-(4-pyridyl)imidazoleHCID 178418339Butyllithium

생성물 1

HCID 187715342-Formyl-1-methyl-4-phenyl-5-[4-pyridyl]imidazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-methyl-4-phenyl-5-[4-pyridinyl]imidazole (0.275 g, 1.17 mmol) in THF at −78° C. was added n-butyllithium (0.56 mL of 2.5 M solution, 1.40 mmol). The resulting red-orange solution was allowed to stir at −78° C. for 0.5 h when DMF (0.18 mL, 2.34 mmol) was added. The mixture was allowed to warm to rt and stir for 4 h, then quenched with ice water and partitioned between CH2Cl2 and H2O. The organic extract was washed with aqueous NaCl and dried (MgSO4).The solvent was removed in vacuo and the residue was purified by flash chromatography eluting with 50:1 CH2Cl2/MeOH. The title compound was obtained as a white solid (0.187 g, 61%): mp 167-168° C.

후처리

  1. additionwas added
  2. customquenched with ice water
  3. custompartitioned between CH2Cl2 and H2O
  4. extractionThe organic extract
  5. washwas washed with aqueous NaCl
  6. dry with materialdried (MgSO4).The solvent
  7. customwas removed in vacuo
  8. customthe residue was purified by flash chromatography
  9. washeluting with 50:1 CH2Cl2/MeOH

출처 및 근거

ORD 기록
ord-0591f931e7a94c46bffc1f6d41dccede
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06645989B2

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