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4-Bromotoluene → 5-(Benzyloxy)-3-p-tolyl-3H-imidazo[4,5-b]pyridine

HRID 1890343
ノート
印刷プレビュー

反応式

HRID 1890343 の反応式
[CH2:1]([O:8][C:9]1[N:14]=[C:13]2[NH:15][CH:16]=[N:17][C:12]2=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].C(OC1N=C2N=CN(C3C=CC(C)=CC=3)C2=CC=1)C1C=CC=CC=1>CCOC(C)=O.[Cu]I.CN1C(=O)CCC1>[CH2:1]([O:8][C:9]1[N:14]=[C:13]2[N:15]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[CH:16]=[N:17][C:12]2=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 78054-BromotolueneHCID 11430Potassium CarbonateHCID 673139335-(benzyloxy)-1-p-tolyl-1H-imidazo[4,5-b]pyridineHCID 178420377HCID 178420377、化合物

生成物 1

HCID 673118605-(Benzyloxy)-3-p-tolyl-3H-imidazo[4,5-b]pyridine

試薬・触媒・溶媒 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 8857Ethyl Acetate溶媒
HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

5-(Benzyloxy)-3H-imidazo[4,5-b]pyridine (0.204 g, 0.906 mmol), 4-bromotoluene (0.123 mL, 0.996 mmol), potassium carbonate (263 mg, 1.90 mmol), copper(1) iodide (8.6 mg, 0.045 mmol) and NMP (3 mL) were heated at 210° C. for 1 h under microwave irradiation in a heavy walled sealed tube. The mixture was cooled to room temperature and diluted with EtOAc. The solution was washed with water and the organics were dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography to give a mixture of the title compound and its regioisomer 5-(benzyloxy)-1-p-tolyl-1H-imidazo[4,5-b]pyridine (154 mg). LCMS m/z=316.3 [M+H]+.

後処理

  1. washThe solution was washed with water
  2. dry with materialthe organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography
  6. customto give

出典と根拠

ORDレコード
ord-b840706e0710458a8b41e377659c3ad1
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08507473B2

反応ノート

読み込み中…

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