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Stannane, tributyl(1-ethoxyethenyl)- → 1-(3-(Quinolin-6-ylmethyl)imidazo[1,2-a]pyrimidin-6-yl)ethanone

HRID 456119
ノート
印刷プレビュー

反応式

HRID 456119 の反応式
Br[C:2]1[CH:3]=[N:4][C:5]2[N:6]([C:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)=[CH:9][N:10]=2)[CH:7]=1.BrC1C=NC2N(C=C(CC3C=C4C(=CC=3)N=CC=C4)N=2)C=1.C([Sn](CCCC)(CCCC)[C:48]([O:50]CC)=[CH2:49])CCC>O1CCOCC1.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:18]1[C:19]2[C:14](=[CH:13][C:12]([CH2:11][C:8]3[N:6]4[CH:7]=[C:2]([C:48](=[O:50])[CH3:49])[CH:3]=[N:4][C:5]4=[N:10][CH:9]=3)=[CH:21][CH:20]=2)[CH:15]=[CH:16][CH:17]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 581904746-((6-Bromoimidazo[1,2-a]pyrimidin-3-yl)methyl)quinolineHCID 669271896-(6-Bromo-imidazo[1,2-a]pyrimidin-2-ylmethyl)quinoline

生成物 1

HCID 581904831-(3-(Quinolin-6-ylmethyl)imidazo[1,2-a]pyrimidin-6-yl)ethanone

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物
触媒
HCID 8857Ethyl Acetate溶媒
HCID 312751,4-Dioxane溶媒

実験手順

A solution of 6-((6-bromoimidazo[1,2-a]pyrimidin-3-yl)methyl)quinoline and 6-(6-bromo-imidazo[1,2-a]pyrimidin-2-ylmethyl)quinoline (mixture, 250 mg, 0.737 mmol), PdCl2(PPh3)2 (51.7 mg, 0.074 mmol) and tributyl(1-ethoxyvinyl)stannane (399 mg, 1.106 mmol) in 5 mL of 1,4-dioxane was heated at 80° C. for 12 h under N2. The reaction mixture was diluted with EtOAc, washed with water. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was dissolved in HOAc and 3 N HCl and stirred at room temperature for 3 hours. The solvent was removed under reduced pressure and the residue was dissolved in CH2Cl2, washed with sat. aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography in silica gel eluting with a EtOAc/MeOH gradient to afford the title compound as a yellow solid. 1H-NMR (400 MHz, CDCl3) δ ppm 8.97 (d, 1H), 8.84 (d, 1H), 8.67 (d, 1H), 8.04-7.99 (m, 2H), 7.74 (s, 1H), 7.53-7.51 (m, 1H), 7.34 (dd, 1H), 7.19 (s, 1H), 4.44 (s, 2H), 2.49 (s, 3H).

後処理

  1. washwashed with water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in HOAc
  6. customThe solvent was removed under reduced pressure
  7. dissolutionthe residue was dissolved in CH2Cl2
  8. washwashed with sat. aqueous NaHCO3 and brine
  9. dry with materialThe organic layer was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by flash chromatography in silica gel eluting with a EtOAc/MeOH gradient

出典と根拠

ORDレコード
ord-507f53d632aa401da6a2c6e35b36d5aa
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08497368B2

反応ノート

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