Diisopropylethylamine → 4-(2-Chloro-6-iodopyridin-3-yloxy)-6,7-dimethoxyquinoline

HRID 1433489ノート

反応式

HRID 1433489 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Cl:16][C:17]1[C:22]([OH:23])=[CH:21][CH:20]=[C:19]([I:24])[N:18]=1.C(N(C(C)C)CC)(C)C.C(OCC)(=O)C.O1CCCC1>CN(C)C=O.CCCCCC.C(OCC)(=O)C.O>[Cl:16][C:17]1[C:22]([O:23][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:21][CH:20]=[C:19]([I:24])[N:18]=1

参加物

9

反応物 4

HCID 81531DiisopropylethylamineHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 107774172-Chloro-3-hydroxy-6-iodopyridineHCID 21939870Tetrahydrofuran ethyl acetate

生成物 1

HCID 229365854-(2-Chloro-6-iodopyridin-3-yloxy)-6,7-dimethoxyquinoline収率 49%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

4-Chloro-6,7-dimethoxyquinoline (2.23 g, 10.0 mmol), 2-chloro-6-iodopyridin-3-ol (2.55 g, 22.0 mmol) and diisopropylethylamine (1.29 g, 10.0 mmol) were heated and stirred in dimethylformamide (5 ml) at 130° C. for 3 hours. The reaction solution was distributed between an ethyl acetate-tetrahydrofuran mixed solvent and water, the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent—ethyl acetate:hexane=3:1), and the fraction containing the target substance was concentrated, suspended in ethyl acetate and diluted with hexane, after which the crystals were filtered out, washed with hexane and then blow-dried to obtain the title compound (2.16 g, 4.88 mmol, 49%) as colorless crystals.

後処理

  1. washthe organic layer was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe drying agent was filtered off
  4. distillationthe filtrate was distilled off under reduced pressure
  5. customThe obtained crude product
  6. additionthe fraction containing the target substance
  7. concentrationwas concentrated
  8. additiondiluted with hexane
  9. filtrationafter which the crystals were filtered out
  10. washwashed with hexane
  11. customblow-dried

出典と根拠

ORDレコード
ord-12dd3267da1e4701ad8e954ba54c2698
出典データセット
uspto-grants-2009_11
特許番号
US07612092B2

反応ノート

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