Tetrahydrofuran → 2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-carbaldehyde

HRID 923753

반응식

HRID 923753 반응식
Br[C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[S:17][CH2:18][CH3:19])[N:8]([CH3:20])[C:5]2=[N:6][CH:7]=1.C1C[O:24][CH2:23]C1.C([Li])CCC.[Cl-].[NH4+]>C(=O)=O.CC(C)=O.CN(C=O)C>[CH2:18]([S:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:9]1[N:8]([CH3:20])[C:5]2=[N:6][CH:7]=[C:2]([CH:23]=[O:24])[CH:3]=[C:4]2[N:10]=1)[CH3:19]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 679820336-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridineHCID 178418339Butyllithium

생성물 1

HCID 867082082-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-carbaldehyde

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 18522661Acetone cardice용매

실험 절차

To a mixture of 6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (2 g) and THF (60 ml), n-butyllithium (1.6 M in hexane) (4.3 ml) was added dropwise with cooling in dry-ice-acetone bath. The mixture was stirred for 30 minutes, and then DMF (2.2 ml) was poured. The mixture was heated to room temperature, and then saturated aqueous ammonium chloride solution was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated tinder reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 189 mg of 2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-carbaldehyde (hereinafter referred to as Present Compound 51).

후처리

  1. additionwas added dropwise
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated tinder reduced pressure

출처 및 근거

ORD 기록
ord-966419a00aa94cbea732f715f588bc03
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278983B2

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