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Lithium Chloride → 2-(2-methyl-allyl)-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

HRID 1773878
ノート
印刷プレビュー

反応式

HRID 1773878 の反応式
I[C:2]1[N:11]=[C:10]2[N:4]([CH2:5][CH2:6][C:7]3[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=3[CH:9]2[O:12][CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)[CH:3]=1.[CH2:24]([Sn](CCCC)(CCCC)CCCC)[C:25](=[CH2:27])[CH3:26].[Li+].[Cl-].[F-].[K+]>CN(C=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:26][C:25](=[CH2:24])[CH2:27][C:2]1[N:11]=[C:10]2[N:4]([CH2:5][CH2:6][C:7]3[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=3[CH:9]2[O:12][CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)[CH:3]=1
参加物反応条件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 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 11013379Methallyltri-n-butyltinHCID 726957782-iodo-4-(1-methyl piperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

生成物 1

HCID 726946772-(2-methyl-allyl)-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2-iodo-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene (example 2A) (100 mg, 0.24 mmoles) in DMF (4 mL) in a screw-capped vial under argon are added methallyltributyltin (331 mg, 0.96 mmole), Pd(PPh3)4 (28 mg, 24 μmole), LiCl (51 mg, 1.2 mmoles). The reaction mixture is heated at 80° C. for 5 hours. A solution of 10% KF in water is added, and the aqueous phase is extracted three times with CH2Cl2. The organic phase is washed with a solution of 10% KF in water, brine, dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel chromatography using (CH2Cl2:MeOH:NH4OH) as eluent with a gradient from (98:2:0.2) to (96.5:3.5:0.35). As the residue is contaminated with tin salts, 1N aqueous HCl is added, and the aqueous phase is extracted three times with Et2O. The aqueous phase is basified to pH 10 with 12N NaOH and the aqueous phase is extracted three times with AcOEt. The organic phase is dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure to afford 2-(2-methyl-allyl)-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene.

後処理

  1. extractionthe aqueous phase is extracted three times with CH2Cl2
  2. washThe organic phase is washed with a solution of 10% KF in water, brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent is removed under reduced pressure
  6. customThe residue is purified by silica gel chromatography
  7. additionis added
  8. extractionthe aqueous phase is extracted three times with Et2O
  9. extractionthe aqueous phase is extracted three times with AcOEt
  10. dry with materialThe organic phase is dried over magnesium sulphate
  11. filtrationfiltered
  12. customthe solvent is removed under reduced pressure

出典と根拠

ORDレコード
ord-51c1290fe07f4bd29f8cbf2781d0d0af
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09255101B2

反応ノート

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