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Potassium Carbonate → [5-(4-Benzyloxy-3-fluoro-phenyl)-6-chloro-1H-benzimidazol-2-ylsulfanyl]-acetic acid tert-butyl ester

HRID 1045105
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1045105
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][C:10]=1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:23][C:24](=[O:38])[CH2:25][S:26][C:27]1[NH:31][C:30]2[CH:32]=[C:33]([Cl:37])[C:34](I)=[CH:35][C:29]=2[N:28]=1)([CH3:22])([CH3:21])[CH3:20].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.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:19]([O:23][C:24](=[O:38])[CH2:25][S:26][C:27]1[NH:31][C:30]2[CH:32]=[C:33]([Cl:37])[C:34]([C:12]3[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[C:10]([F:18])[CH:11]=3)=[CH:35][C:29]=2[N:28]=1)([CH3:22])([CH3:20])[CH3:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 27377884-Benzyloxy-3-fluorophenylboronic AcidHCID 58387110Tert-butyl 2-(6-chloro-5-iodo-1H-benzo[d]imidazol-2-ylthio)acetate2×

Produkt 1

HCID 58387185[5-(4-Benzyloxy-3-fluoro-phenyl)-6-chloro-1H-benzimidazol-2-ylsulfanyl]-acetic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A 4 mL vial with a septum cap and a stirring bar was charged with 4-benzyloxy-3-fluoro-phenylboronic acid (14.8 mg, 0.060 mmol) and Pd(PPh3)4 (5.8 mg, 5 mol %) and was purged briefly with N2. A solution of (6-chloro-5-iodo-1H-benzoimidazol-2-ylsulfanyl)-acetic acid tert-butyl ester (Intermediate 4, 21.4 mg, 0.050 mmol) in toluene (200 uL) was added to the vial, followed by a solution K2CO3 (21.4 mg, 0.050 mmol) in water (100 uL). The resulting mixture was stirred at 80° C. for 14 h. The mixture was allowed to cool down to rt, and was partitioned with EtOAc (1 mL) and 10% aqueous AcOH (1 mL). The organic layer was separated evaporated to dryness in vacuo. LR-MS (API-ES) of the residue confirmed the presence of the title compound: calculated for C26H24ClFN2O3S 498.1, observed m/e 499.0 (M+H)+ (Rt 3.54 min). The crude product was used in the next step without further purification.

Aufarbeitung

  1. customA 4 mL vial with a septum cap
  2. customwas purged briefly with N2
  3. temperatureto cool down to rt
  4. customwas partitioned with EtOAc (1 mL) and 10% aqueous AcOH (1 mL)
  5. customThe organic layer was separated
  6. customevaporated to dryness in vacuo
  7. customThe crude product was used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-71ab1517df124420bf568b5d47a7daa8
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08563746B2

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