Dimethylformamide → HCID 178456234, Verbindung

HRID 78498

Reaktionsgleichung

Reaktionsgleichung von HRID 78498
[C:1]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CN(C)C=O.[CH3:27][C:28](C)([O-])[CH3:29].[K+].C(Br)C=C>O1CCCC1>[CH2:29]([N:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[S:9]/[C:8]/1=[N:10]\[C:11](=[O:21])[C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[O:19][CH3:20])[CH:28]=[CH2:27]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 23665647Potassium tert-butoxideHCID 87094486n-(5-Tert-butylthiazol-2-yl)-5-chloro-2-methoxybenzamide

Produkt 1

HCID 178456234HCID 178456234, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of Example 244A (410 mg, 1.3 mmol) in 5 mL of tetrahydrofuran:N,N-dimethylformamide (4/1) at 0° C. was added potassium tert-butoxide (230 mg, 1.9 mmol). The reaction mixture was stirred for 1 hour then allyl bromide (0.16 mL, 1.9 mmol) was added. The mixture was warmed to 65° C. and stirred overnight. The mixture was cooled to ambient temperature, concentrated, diluted with CH2Cl2 and washed with water and brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by chromatography (20-50% ethyl ccetate/hexane gradient) afforded the title compound. 1H NMR (CDCl3, 300 MHz) δ ppm 1.34 (s, 9H), 3.90 (s, 3H), 4.78-4.85 (m, 3H), 5.22-5.36 (m, 2H), 5.90-6.09 (m, J=17.0, 10.17 Hz, 1H), 6.62 (s, 1H), 6.90 (d, J=9.2 Hz, 1H), 7.32 (dd, J=8.8, 3.1 Hz, 1H), 8.00 (d, J=2.7 Hz, 1H); MS (DCI/NH3) m/z 365 (M+H)+.

Aufarbeitung

  1. stirringstirred overnight
  2. temperatureThe mixture was cooled to ambient temperature
  3. concentrationconcentrated
  4. additiondiluted with CH2Cl2
  5. washwashed with water and brine
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification by chromatography (20-50% ethyl ccetate/hexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-d3cd82d018ef49379c04b7d341157a9b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841334B2

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