8-Hydroxyquinoline → HCID 56941125、化合物

HRID 1843994ノート

反応式

HRID 1843994 の反応式
[C:1]1(=[O:14])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][NH:2]1.I[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:21]=1[CH3:22].OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.[Cu]I.CO.CS(C)=O>[CH3:22][C:21]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[N:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]=2[C:1]1=[O:14]

参加物

9

反応物 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 121012772,5-dihydro-1H-pyrido[4,3-b]indol-1-oneHCID 144235133-Iodo-4-methylpyridine

生成物 1

HCID 56941125HCID 56941125、化合物収率 5.4%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
150 °C

実験手順

2,5-dihydro-1H-pyrido[4,3-b]indol-1-one (I-62a: 500 mg, 2.71 mmol), 3-iodo-4-methylpyridine (892 mg, 4 mmol), 8-hydroxy quinoline (79 mg, 0.542 mmol) and K2CO3 (560 mg, 4.06 mmol) were added to a previously degassed solution of DMSO (10 mL). This was followed by the addition of CuI (103.2 mg, 0.542 mmol) and the resulting reaction mass was heated at 150° C. for 16 hours in a sealed tube. The reaction was monitored by TLC (5% methanol in DCM). The reaction mass was quenched with water, diluted using ethyl acetate and filtered. The filtrate was extracted using ethyl acetate, washed the organic layer with water, brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (1% methanol in DCM), followed by preparative HPLC afforded 40 mg of the product (5.4% yield).

後処理

  1. customthe resulting reaction mass
  2. customThe reaction mass was quenched with water
  3. additiondiluted
  4. filtrationfiltered
  5. extractionThe filtrate was extracted
  6. washwashed the organic layer with water, brine solution
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customto afford the crude product
  10. customPurification by column chromatography on silica gel (1% methanol in DCM)

出典と根拠

ORDレコード
ord-a48d2795cbd54e9a82aea4a5283e85f0
出典データセット
uspto-grants-2015_02
特許番号
US08946260B2

反応ノート

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