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Iodide Ion → 6-Chloro-3-(1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethyl)imidazo[1,2-b]pyridazine

HRID 1942050
ノート
印刷プレビュー

反応式

HRID 1942050 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][C:22]=3[F:23])[N:19]([CH3:24])[N:18]=[CH:17]4)(O)[CH3:12])=[CH:9][N:10]=2)[N:7]=1.[I-].O[PH2]=O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][C:22]=3[F:23])[N:19]([CH3:24])[N:18]=[CH:17]4)[CH3:12])=[CH:9][N:10]=2)[N: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

5

反応物 3

HCID 30165Iodide IonHCID 4124402Phosphinic AcidHCID 581475401-(6-Chloroimidazo[1,2-b]pyridazin-3-yl)-1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethanol

生成物 1

HCID 581475176-Chloro-3-(1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethyl)imidazo[1,2-b]pyridazine

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

(rac)-1-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-1-(6-fluoro-1-methyl-1H-indazol-5-yl)-ethanol ((i), 21.4 g, 61.9 mmol) was dissolved in acetic acid (310 mL) and introduced in 20 microwave reactor-vials. Iodide (2.36 g×20, 186 mmol), followed by H3PO2 50% (2.56 mL×20, 464 mmol) were then added into each vial. Then they were submitted to microwave irradiations 10 min at 150° C. The combined RMs were concentrated in vacuo and the residue was diluted with water, basified by a 4 M NaOH solution and extracted twice with EtOAc. The organics were joined and washed with brine, dried over Na2SO4 and the solvent was removed. The residue was triturated with diisopropyl ether. The precipitate formed was filtered off to give a beige solid (tR 4.08 min (conditions 1), tR 14.39/16.40 min (conditions 2), MH+=330, 1H-NMR in DMSO-d6: 8.19 (d, 1H); 7.92 (s, 1H); 7.80 (s, 1H); 7.55 (d, 1H); 7.42 (d, 1H); 7.28 (d, 1H); 4.84 (m, 1H); 3.96 (s, 3H); 1.71 (d, 3H)).

後処理

  1. additionintroduced in 20 microwave reactor-vials
  2. additionwere then added into each vial
  3. customirradiations 10 min
  4. customat 150° C
  5. concentrationThe combined RMs were concentrated in vacuo
  6. additionthe residue was diluted with water
  7. extractionextracted twice with EtOAc
  8. washwashed with brine
  9. dry with materialdried over Na2SO4
  10. customthe solvent was removed
  11. customThe residue was triturated with diisopropyl ether
  12. customThe precipitate formed
  13. filtrationwas filtered off
  14. customto give a beige solid (tR 4.08 min (conditions 1)
  15. custom16.40 min (conditions 2), MH+=330, 1H-NMR in DMSO-d6: 8.19 (d, 1H); 7.92 (s, 1H); 7.80 (s, 1H); 7.55 (d, 1H); 7.42 (d, 1H); 7.28 (d, 1H); 4.84 (m, 1H); 3.96 (s, 3H); 1.71 (d, 3H)

出典と根拠

ORDレコード
ord-625ea207a68c49ef83b96d2105d3e908
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08389526B2

反応ノート

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