Potassium Carbonate → (S)-tert-butyl 4-(3-(6-(1-tert-butoxy-2-methoxy-2-oxoethyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-2-yl)phenyl)piperazine-1-carboxylate

HRID 879625Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 879625
Br[C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:9]([C@H:18]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:19]([O:21][CH3:22])=[O:20])[C:8]([CH3:28])=[CH:7][C:5]=2[N:6]=1.CC1(C)C(C)(C)OB([C:37]2[CH:38]=[C:39]([N:43]3[CH2:48][CH2:47][N:46]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:45][CH2:44]3)[CH:40]=[CH:41][CH:42]=2)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Cl-].[Na+].O.CCOC(C)=O.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>[C:24]([O:23][C@@H:18]([C:9]1[C:8]([CH3:28])=[CH:7][C:5]2[N:6]=[C:2]([C:37]3[CH:38]=[C:39]([N:43]4[CH2:44][CH2:45][N:46]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:47][CH2:48]4)[CH:40]=[CH:41][CH:42]=3)[S:3][C:4]=2[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:19]([O:21][CH3:22])=[O:20])([CH3:27])([CH3:26])[CH3:25]

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 16414220tert-Butyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine-1-carboxylateHCID 86699809Methyl (S)-2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-(tert-butoxy)acetate

Produkt 1

HCID 86700435(S)-tert-butyl 4-(3-(6-(1-tert-butoxy-2-methoxy-2-oxoethyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-2-yl)phenyl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

To a solution of (S)-methyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (193 mg, 0.40 mmol) and tert-butyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine-1-carboxylate (217 mg, 0.56 mmol) in 1,4-dioxane (3 mL) was added potassium carbonate solution (0.80 mL, 1.6 mmol, 2 M aqueous solution) and Pd(PPh3)4 (23 mg, 0.02 mmol). The reaction mixture was stirred at 105° C. for 3 h. The mixture was diluted with brine (5 mL) and EtOAc (5 mL). The layers were separated, and the organic layer was dried, filtered, and concentrated in vacuo and used without further purification. LCMS-ESI+: calc'd for C36H43ClN3O5S: 664.3 (M+H+); Found: 664.3 (M+H+).

Aufarbeitung

  1. customThe layers were separated
  2. customthe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customused without further purification

Quellen und Nachweise

ORD-Eintrag
ord-682040b414da4de3a7696e04456d204a
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987250B2

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