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

HRID 923753

反応式

HRID 923753 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 18522661Acetone cardice溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-966419a00aa94cbea732f715f588bc03
出典データセット
uspto-grants-2016_03
特許番号
US09278983B2

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