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Ethanol → HCID 145857641, Verbindung

HRID 2216197
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2216197
[CH3:1][Si:2]([CH3:27])([CH3:26])[CH2:3][CH2:4][O:5][C:6](=[O:25])[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11](B2OC(C)(C)C(C)(C)O2)=[C:10]([NH2:24])[CH:9]=1.[C:28]([O:32][C:33](=[O:54])[NH:34][C:35]([C:37]1[S:38][C:39]([S:52][CH3:53])=[C:40]([S:42]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47](Br)[CH:46]=2)(=[O:44])=[O:43])[CH:41]=1)=[NH:36])([CH3:31])([CH3:30])[CH3:29].C([O-])([O-])=O.[Na+].[Na+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.CCOC(C)=O.C1(C)C=CC=CC=1>[CH3:27][Si:2]([CH3:1])([CH3:26])[CH2:3][CH2:4][O:5][C:6](=[O:25])[NH:7][C:8]1[CH:9]=[C:10]([NH2:24])[C:11]([C:49]2[CH:48]=[CH:47][CH:46]=[C:45]([S:42]([C:40]3[CH:41]=[C:37]([C:35]([NH:34][C:33]([O:32][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:54])=[NH:36])[S:38][C:39]=3[S:52][CH3:53])(=[O:43])=[O:44])[CH:50]=2)=[C:12]([CH3:14])[CH:13]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 57532218HCID 57532218, VerbindungHCID 145857672tert-butyl N-[4-(3-bromophenyl)sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Produkt 1

HCID 145857641HCID 145857641, VerbindungAusbeute 55,5 %

Reagenzien, Katalysatoren, Lösungsmittel

4
HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A flask with a stirbar was charged with [3-amino-5-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-carbamic acid 2-trimethylsilanyl-ethyl ester ((Example 294: step e) 2.34 g, 5.96 mmol), {[4-(3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester ((Example 27: step c) 2.93 g, 5.96 mmol), aqueous Na2CO3 (2M, 11.9 mL, 23.8 mmol), ethanol (12 mL) and toluene (24 mL). The solution was sparged with argon for 10 min and Pd(PPh3)4 (689 mg, 0.6 mmol) was added. The biphasic solution was vigorously stirred under inert atmosphere at 80° C. for 16 h, then was cooled to rt. EtOAc (80 mL) and water (20 mL) were added and the layers were separated. The organic layer was washed with saturated NaHCO3 (2×20 mL), brine (20 mL) and was dried over sodium sulfate. Removal of the solvents in vacuo followed by column chromatography (85:15 DCM/EtOAc) of the residue yielded the title compound (2.24 g, 55%) as a light brown solid. 1H-NMR (CDCl3): δ 7.98 (ddd, 1H, J=1.3, 1.9, 7.8 Hz), 7.89 (m, 2H), 7.61 (t, 1H, J=7.7 Hz), 7.5 (dt, 1H, J=1.3, 7.7 Hz), 6.88 (s, 1H), 6.55 (d, 1H, J=1.7 Hz), 6.47 (s, 1H), 4.26 (m, 2H), 3.42 (s, 2H), 2.56 (s, 3H), 1.9 (s, 3H), 1.52 (s, 9H), 1.06 (m, 2H), 0.08 (s, 9H).

Aufarbeitung

  1. customThe solution was sparged with argon for 10 min
  2. temperaturewas cooled to rt
  3. customthe layers were separated
  4. washThe organic layer was washed with saturated NaHCO3 (2×20 mL), brine (20 mL)
  5. dry with materialwas dried over sodium sulfate
  6. customRemoval of the solvents in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ef52491c304343e18555a8a10feeb7b0
Quelldatensatz
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07109354B2

Notizen zur Reaktion

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