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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
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HRID 1773878 반응식
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
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참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매
HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-51c1290fe07f4bd29f8cbf2781d0d0af
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09255101B2

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