Phenyl chloroformate → Phenyl [5-cyano-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carbamate

HRID 57194Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57194
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[NH2:11][C:12]1([C:38]2[C:39]([O:44][CH2:45][CH3:46])=[N:40][CH:41]=[CH:42][CH:43]=2)[C:20]2[C:15](=[CH:16][C:17]([F:23])=[C:18]([C:21]#[N:22])[CH:19]=2)[N:14]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=2[O:35][CH3:36])(=[O:26])=[O:25])[C:13]1=[O:37]>N1C=CC=CC=1>[C:21]([C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][C:17]=1[F:23])[N:14]([S:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=1[O:35][CH3:36])(=[O:25])=[O:26])[C:13](=[O:37])[C:12]2([NH:11][C:2](=[O:3])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:38]1[C:39]([O:44][CH2:45][CH3:46])=[N:40][CH:41]=[CH:42][CH:43]=1)#[N:22]

Komponenten

4

Edukt 2

HCID 15891Phenyl chloroformateHCID 670877293-Amino-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile

Produkt 1

HCID 86725451Phenyl [5-cyano-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carbamateAusbeute 71,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

61 μl (0.49 mmol) of phenyl chloroformate were slowly added dropwise to a solution, cooled to 0° C., of 226 mg (0.44 mmol) of 3-amino-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile in 4 ml of pyridine. After 5 minutes, the solvent was evaporated. The residue was mixed with 20 ml of water and extracted with diethyl ether (2×). The organic phase was washed with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (Redisep cartridge, mobile phase gradient from 0 to 5% methanol in ethyl acetate). 200 mg of the title compound were obtained.

Aufarbeitung

  1. customthe solvent was evaporated
  2. additionThe residue was mixed with 20 ml of water
  3. extractionextracted with diethyl ether (2×)
  4. washThe organic phase was washed with water and saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel (Redisep cartridge, mobile phase gradient from 0 to 5% methanol in ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1ed35a49a8474c459235ac9e3e48e4d7
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434713B2

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