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Potassium Carbonate → HCID 86700342, Verbindung

HRID 879523
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 879523
[C:1]([O:5][C@@H:6]([C:12]1[C:28]([CH3:29])=[CH:27][C:15]2[N:16]=[C:17]([C:19]3[C:24]([F:25])=[CH:23][N:22]=[C:21](Cl)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:37][N:38]1[C:46]2[C:41](=[CH:42][C:43](B(O)O)=[CH:44][CH:45]=2)[CH:40]=[N:39]1.C([O-])([O-])=O.[K+].[K+]>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:1]([O:5][C@@H:6]([C:12]1[C:28]([CH3:29])=[CH:27][C:15]2[N:16]=[C:17]([C:19]3[C:24]([F:25])=[CH:23][N:22]=[C:21]([C:43]4[CH:42]=[C:41]5[C:46](=[CH:45][CH:44]=4)[N:38]([CH3:37])[N:39]=[CH:40]5)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:2])[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 225589101-Methyl-1H-indazole-5-boronic acidHCID 86700343(S)-ethyl 2-(tert-butoxy)-2-(2-(2-chloro-5-fluoropyridin-4-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)acetate

Produkt 1

HCID 86700342HCID 86700342, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A microwave vial containing (S)-ethyl 2-(tert-butoxy)-2-(2-(2-chloro-5-fluoropyridin-4-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)acetate (22 mg, 0.04 mmol) was charged with (1-methyl-1H-indazol-5-yl)boronic acid (19 mg, 0.11 mmol), then Pd(PPh3)4 (9 mg, 0.008 mmol). The vial was flushed with argon, diluted with dioxane (2.0 mL) and to this was added 2M aqueous K2CO3 (0.10 mL, 0.20 mmol). The vial was sealed, heated to 120° C. for 3 hours, and then allowed to cool to room temperature. The mixture was diluted with EtOAc, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by silica gel column chromatography (10-40% EtOAc/Hex gradient) to afford the desired product. LCMS-ESI+: calc'd for C35H33ClFN4O3S: 643.2 (M+H+); Found: 643.2 (M+H+).

Aufarbeitung

  1. customThe vial was flushed with argon
  2. additiondiluted with dioxane (2.0 mL)
  3. customThe vial was sealed
  4. temperatureto cool to room temperature
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by silica gel column chromatography (10-40% EtOAc/Hex gradient)

Quellen und Nachweise

ORD-Eintrag
ord-7705ddc99343481582b3e8595939e066
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08987250B2

Notizen zur Reaktion

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