Potassium tert-butoxide → 6-chloro-1H-indole-5-carbonitrile

HRID 475273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475273
[NH2:1][C:2]1[C:9]([C:10]#[CH:11])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:12])[CH:3]=1.CC([O-])(C)C.[K+]>C1COCC1>[Cl:12][C:4]1[CH:3]=[C:2]2[C:9]([CH:10]=[CH:11][NH:1]2)=[CH:8][C:5]=1[C:6]#[N:7]

Komponenten

4

Edukt 2

HCID 23665647Potassium tert-butoxideHCID 866947484-Amino-2-chloro-5-ethynylbenzonitrile

Produkt 1

HCID 748905826-chloro-1H-indole-5-carbonitrileAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a solution of 240 (50 mg, 0.284 mmol) in THF (100 mL) was added t-BuOK (160 mg, 1.42 mmol). The mixture was heated at 75° C. for 3 h during which the color of the reaction mixture changed from yellow to brown. After the mixture was cooled, it was partitioned between EtOAc (200 mL) and H2O (50 mL). The organic layer was separated, washed with brine, dried and concentrated in vacuo to afford 43 mg (86%) of 6-chloro-1H-indole-5-carbonitrile (242) as white solid: 1H NMR (500 MHz, DMSO-d6) (511.80 (s, 1H), 8.21 (s, 1H), 7.70 (s, 1H), 7.60 (d, 1H), 6.61 (d, 1H); MS (ESI) m/z=177.0 [M+1]+.

Aufarbeitung

  1. temperatureAfter the mixture was cooled
  2. customit was partitioned between EtOAc (200 mL) and H2O (50 mL)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3667633bd8364d6cb417c7ede19dd692
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637537B2

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