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Dimethylformamide → 6-(4-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine

HRID 331018
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 331018
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH3:12])[CH:9]=[C:10](I)[C:3]=12.[CH3:13][N:14]1[CH2:19][CH2:18][O:17][C:16]2[CH:20]=[CH:21][C:22](B3OC(C)(C)C(C)(C)O3)=[CH:23][C:15]1=2.C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C>C(#N)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH3:12])[CH:9]=[C:10]([C:22]3[CH:21]=[CH:20][C:16]4[O:17][CH2:18][CH2:19][N:14]([CH3:13])[C:15]=4[CH:23]=3)[C:3]=12
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 547587584-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazineHCID 710901484-bromo-3-iodo-1-methyl-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 710901456-(4-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine
Ausbeute 40,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a suspension of 4-bromo-3-iodo-1-methyl-1H-pyrrolo[2,3-b]pyridine (D7) (300 mg, 0.890 mmol) and 4-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine (353 mg, 1.283 mmol) in ACN (2.5 mL) was added 2M sodium carbonate aqueous solution (4.72 mL, 9.43 mmol). DMF (4 mL) and DCM (3 mL) were added to aid the solubility. Then, bis(triphenylphosphine)palladium(II)chloride (81 mg, 0.116 mmol) was added and the reaction was stirred at 55° C. for 30 mins. Volatiles were removed by evaporation before partitioning between DCM and water. The organic layer was separated, dried and concentrated. The crude material was purified on silica eluting with gradient of 0-40% ethyl acetate in cyclohexane to afford the title compound (130 mg). LCMS (A): m/z (M+H)+ 358/360, C17H16BrN3O requires 357/359 (acidic).

Aufarbeitung

  1. customVolatiles were removed by evaporation
  2. custombefore partitioning between DCM and water
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customThe crude material was purified on silica eluting with gradient of 0-40% ethyl acetate in cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-7b35ae86a6d149caa4e85bf45e555a4a
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08877742B2

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