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Toluene → HCID 25260912, Verbindung

HRID 1093299
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1093299
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[N:14]=[C:13](Cl)[N:12]=[C:11]3[N:16]([CH:19]4[CH2:24][CH2:23][N:22]([C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]4)[N:17]=[CH:18][C:10]=13)[CH2:2]2.[C:31]1(C)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[NH2:38]OB(C1C=CC=CC=1)O.C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[NH2:38][C:31]1[CH:36]=[CH:35][C:34]([C:13]2[N:12]=[C:11]3[N:16]([CH:19]4[CH2:20][CH2:21][N:22]([C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24]4)[N:17]=[CH:18][C:10]3=[C:9]([N:3]3[CH2:4][CH:5]4[O:8][CH:1]([CH2:7][CH2:6]4)[CH2:2]3)[N:14]=2)=[CH:33][CH:32]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 57227478HCID 57227478, VerbindungHCID 86629384HCID 86629384, Verbindung

Produkt 1

HCID 25260912HCID 25260912, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

isopropyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate (680 mg, 1.56 mmol) was dissolved in ethanol (8 mL) and toluene (8 mL) and divided over two microwave vials. To each vial was added 1.3 eq of aminophenylboronic acid, pinacol ester (220 mg, 1 mmol to each vial) and a 2M aqueous solution of Na2CO3 (1.57 mL, 3.14 mmol, 4 eq. to each vial). The vials were purged with nitrogen gas and 10 mol % tetrakis(triphenylphosphine)palladium was added (91 mg to each vial). Each vial was heated under microwave irradiation for 60 minutes. The contents of both vials were combined, diluted with dichloromethane and water and filtered over Celite. The organic phase was washed with brine (2×), dried over MgSO4 and concentrated to give the product as an orange foam, which was used without further purification. MS: 492.3 [M+H], RT 2.31

Aufarbeitung

  1. customThe vials were purged with nitrogen gas and 10 mol % tetrakis(triphenylphosphine)palladium
  2. additionwas added (91 mg to each vial)
  3. temperatureEach vial was heated under microwave irradiation for 60 minutes
  4. additiondiluted with dichloromethane and water
  5. filtrationfiltered over Celite
  6. washThe organic phase was washed with brine (2×)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cc26d16b1d834f75b14b3e9cc03ca8a2
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08129371B2

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