Water → HCID 66954106, Verbindung

HRID 444739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 444739
[C:1]([O:5][C:6]([N:8]1[C:12]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17](=[O:22])[C:16]3([CH3:24])[CH3:23])=[CH:11][CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClS([N:29]=[C:30]=O)(=O)=O.CN(C=O)C.O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:12]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17](=[O:22])[C:16]3([CH3:24])[CH3:23])=[CH:11][CH:10]=[C:9]1[C:30]#[N:29])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 54549067HCID 54549067, Verbindung

Produkt 1

HCID 66954106HCID 66954106, VerbindungAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution 5-(3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-pyrrole-1-carboxylic acid tert-butyl ester (0.39 g, 1.2 mmol) in THF (anhydrous, 9 mL) at −78° C. was added chlorosulfonyl isocyanate (1.15 eq, 0.12 mL, 1.4 mmol). After 120 min, DMF (20 eq, 1.8 mL, 23 mmol) was added and the reaction was allowed to warm to room temperature. The reaction mixture was poured into water (25 mL) and extracted with ethyl acetate (2×50 mL). The organic layers were combined, washed with brine (50 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via flash column chromatography on silica gel (1:3 ethyl acetate/hexane) gave 5-(3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-2-cyanopyrrole-1-carboxylic acid tert-butyl ester (0.21 g, 50%) as a white solid; mp 158.6; 1H NMR (DMSO-d6; 300 MHz): δ 1.27 (s, 6H), 1.33 (s, 9H), 6.40 (d, 1H, J=3.8 Hz), 6.90 (d, 1H, J=8.0 Hz), 7.19 (dd, 1H, J=1.8, 8.0 Hz), 7.30 (d, 1H, J=1.5 Hz), 10.50 (s, 1H). MS m/z 350 (M−H)−. Calcd for C19H22N2O3: C, 68.36; H, 6.02; N, 11.96. Found: C, 66.79; H, 6.03; N, 11.02.

Aufarbeitung

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washwashed with brine (50 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via flash column chromatography on silica gel (1:3 ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-edd1c11ab592482da5cb294dc4b24972
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476262B2

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