2-Bromobenzonitrile → 7-Bromo-3-chloro-1-fluorospiro[chromeno[2,3-c]pyridine-5,1'-isoindol]-3'-amine

HRID 1409505Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1409505
C([Li])CCC.Br[C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[C:9]#[N:10].[Br:15][C:16]1[CH:17]=[C:18]2[C:29](=[CH:30][CH:31]=1)[O:28][C:21]1[C:22]([F:27])=[N:23][C:24]([Cl:26])=[CH:25][C:20]=1[C:19]2=[N:32]S(C(C)(C)C)=O>C1COCC1>[Br:15][C:16]1[CH:17]=[C:18]2[C:19]3([C:11]4[C:8](=[CH:7][CH:14]=[CH:13][CH:12]=4)[C:9]([NH2:10])=[N:32]3)[C:20]3[CH:25]=[C:24]([Cl:26])[N:23]=[C:22]([F:27])[C:21]=3[O:28][C:29]2=[CH:30][CH:31]=1

Komponenten

5

Edukt 3

HCID 162722-BromobenzonitrileHCID 86658361N-(7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-ylidene)-2-methylpropane-2-sulfinamideHCID 178418339Butyllithium

Produkt 1

HCID 866892407-Bromo-3-chloro-1-fluorospiro[chromeno[2,3-c]pyridine-5,1'-isoindol]-3'-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of n-butyllithium (1.6 M in hexane, 0.75 mL, 1.2 mmol, Aldrich) was added dropwise to a solution of 2-bromobenzonitrile (219 mg, 1.2 mmol, Oakwood Products) in THF (30 mL) at −78° C. under nitrogen atmosphere. The reaction mixture was allowed to stir for 5 min at −78° C. Subsequently, a solution of N-(7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-ylidene)-2-methylpropane-2-sulfinamide (400 mg, 0.93 mmol, step 1) in THF (30 mL) was added. After 5 min, the reaction mixture was quenched with aqueous, saturated solution of NH4Cl and EtOAc was added. The organic phase was separated and dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel (55-100% EtOAc/hexanes) to afford the title compound as a yellow solid. MS m/z=431.9 [M+H]+. Calculated for C19H10BrClFN3O: 430.7.

Aufarbeitung

  1. waitAfter 5 min
  2. customthe reaction mixture was quenched with aqueous, saturated solution of NH4Cl and EtOAc
  3. additionwas added
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by flash chromatography on silica gel (55-100% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-4e5bfd54534643e4acde9c0ea850b394
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921363B2

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