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3-Methyl-2-(tributylstannyl)pyridine → 9-Bromo-2-(3-methylpyridin-2-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene

HRID 1530374
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1530374
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][N:11]3[C:7](=[N:8][C:9](I)=[CH:10]3)[C:6]=2[CH:16]=1.[CH3:17][C:18]1[C:19]([Sn](CCCC)(CCCC)CCCC)=[N:20][CH:21]=[CH:22][CH:23]=1>CN(C=O)C.[Cu](I)I>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][N:11]3[C:7](=[N:8][C:9]([C:19]4[C:18]([CH3:17])=[CH:23][CH:22]=[CH:21][N:20]=4)=[CH:10]3)[C:6]=2[CH:16]=1
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Komponenten

5

Edukt 2

HCID 164270983-Methyl-2-(tributylstannyl)pyridineHCID 5820440710-Bromo-2-iodo-5,6-dihydrobenzo[F]imidazo[1,2-D][1,4]oxazepine

Produkt 1

HCID 683125639-Bromo-2-(3-methylpyridin-2-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azuleneAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysator
HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 9-bromo-2-iodo-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene (200 mg, 0.512 mmol), 3-methyl-2-tributylstannanylpyridine (235 mg, 0.614 mmol), Pd2(PPh3)2Cl2 (36 mg, 0.051 mmol) and copper iodide (29 mg, 0.153 mmol) in DMF (4 mL) was purged with nitrogen and then heated at 100° C. for 1 h using microwave irradiation. The reaction mixture was diluted with MeOH (30 mL) and then loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 0.5M NH3/MeOH. The product containing fractions were combined and concentrated in vacuo and the resulting residue was purified by column chromatography (Si-PCC, gradient 0-5% MeOH in EtOAc) affording the title compound as a white solid (135 mg, 74%). LCMS: RT 3.22 min [M+H]+ 355.9/357.9

Aufarbeitung

  1. customwas purged with nitrogen
  2. custommicrowave irradiation
  3. additionThe reaction mixture was diluted with MeOH (30 mL)
  4. washwas washed with MeOH
  5. washthe product eluted with 0.5M NH3/MeOH
  6. additionThe product containing fractions
  7. concentrationconcentrated in vacuo
  8. customthe resulting residue was purified by column chromatography (Si-PCC, gradient 0-5% MeOH in EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-4790dd6a9cc141ce936982a38725ebd9
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09090628B2

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