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Toluene → HCID 86698714, Verbindung

HRID 1054714
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1054714
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1B1OCC(C)(C)CO1.Cl.Br[C:25]1[CH:30]=[CH:29][C:28]([CH:31]2[CH2:34][CH2:33][NH:32]2)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl.C(O)C>[NH:32]1[CH2:33][CH2:34][CH:31]1[C:28]1[CH:29]=[CH:30][C:25]([C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][C:2]=2[Cl:1])[NH:8][CH:7]=[C:6]3[C:11]([O:13][CH3:14])=[O:12])=[CH:26][CH:27]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 86698665methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylateHCID 866987152-(4-bromophenyl)azetidine hydrochloride

Produkt 1

HCID 86698714HCID 86698714, VerbindungAusbeute 379,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418807HCID 178418807, VerbindungKatalysator
HCID 702EthanolLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of methyl 6-Chloro-5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-1H-indole-3-carboxylate (50 mg, 0.16 mmol), 2-(4-bromophenyl)azetidine hydrochloride (400 mg, 1.24 mmol), 2M aqueous potassium carbonate (3.11 mL, 6.22 mmol), toluene (9 mL), and ethanol (3 mL) was sparged with nitrogen for 10 minutes, then treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (46 mg, 0.056 mmol). The reaction mixture was heated to 100° C. and stirred. After 2 hours the reaction was cooled to room temperature, diluted with ethyl acetate, washed with water and saturated brine, dried over magnesium sulfate, filtered and concentrated in vacuo to afford a yellow oil, which was purified by flash chromatography (40 g silica, 0-40% methanol/ethyl acetate (1% TEA modifier), 24 column volumes). Product fractions were combined and concentrated in vacuo to afford the title compound as a yellow solid (207 mg, 49% yield). MS (ES+) 341.2 (M+H)+; 1H NMR (500 MHz, CD3OD) δ 7.98 (d, J=3.90 Hz, 2 H), 7.56 (s, 1 H), 7.41 (s, 4 H), 5.02 (t, J=8.17 Hz, 1 H), 3.84 (s, 3 H), 3.68-3.79 (m, 1 H), 3.34-3.45 (m, 1 H), 2.47-2.66 (m, 2 H).

Aufarbeitung

  1. customwas sparged with nitrogen for 10 minutes
  2. temperatureAfter 2 hours the reaction was cooled to room temperature
  3. washwashed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a yellow oil, which
  8. customwas purified by flash chromatography (40 g silica, 0-40% methanol/ethyl acetate (1% TEA modifier), 24 column volumes)
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fe478e1ef4e447daba58bf47073cf1b4
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09394285B2

Notizen zur Reaktion

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