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Tris(furan-2-yl)phosphane → Tert-butyl cyclopropyl(2-(3-(trifluoromethoxy)phenyl)pyrazolo[1,5-a][1,3,5]triazin-4-yl)carbamate

HRID 2036989
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2036989
[CH:1]1([N:4]([C:12]2[N:17]3[N:18]=[CH:19][CH:20]=[C:16]3[N:15]=[C:14](SC)[N:13]=2)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1.[F:23][C:24]([F:36])([F:35])[O:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>S1C=CC=C1C([O-])=O.[Cu+].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:1]1([N:4]([C:12]2[N:17]3[N:18]=[CH:19][CH:20]=[C:16]3[N:15]=[C:14]([C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([O:25][C:24]([F:23])([F:35])[F:36])[CH:27]=3)[N:13]=2)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 67216767Tert-butyl cyclopropyl(2-(methylthio)pyrazolo[1,5-a][1,3,5]triazin-4-yl)carbamate

Produkt 1

HCID 67216572Tert-butyl cyclopropyl(2-(3-(trifluoromethoxy)phenyl)pyrazolo[1,5-a][1,3,5]triazin-4-yl)carbamateAusbeute 85,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 11194830Cuprous 2-thiophenecarboxylateKatalysator

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Note: THF was degassed with a stream of N2 for 10 min. in a separate flask. Tert-butyl cyclopropyl(2-(methylthio)pyrazolo[1,5-a][1,3,5]triazin-4-yl)carbamate (100 mg, 0.31 mmol), 3-(trifluoromethoxy)phenyl boronic acid (154 mg, 0.74 mmol), tri(2-furyl)phosphine (86 mg, 0.37 mmol), copper(I) thiophene-2-carboxylate (167 mg, 0.88 mmol), Pd2 dba3 (24 mg, 0.03 mmol) were combined. The flask was evacuated and backfilled with N2. THF (3.7 mL) was added and the reaction was heated to 50° C. for 5 d. The solution was diluted with Et2O (40 mL) and washed with 10% NH4OH (3×30 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The solid residue was triturated with Et2O and filtered. The filtrate was concentrated in vacuo and purified via flash column chromatography (2.5-5% EtOAc/hexanes) to afford tert-butyl cyclopropyl(2-(3-(trifluoromethoxy)phenyl)pyrazolo[1,5-a][1,3,5]triazin-4-yl)carbamate (116 mg, 85%). LCMS (ES): >95% pure, m/z 436 [M+1]+.

Aufarbeitung

  1. customTHF was degassed with a stream of N2 for 10 min. in a separate flask
  2. customThe flask was evacuated
  3. additionTHF (3.7 mL) was added
  4. additionThe solution was diluted with Et2O (40 mL)
  5. washwashed with 10% NH4OH (3×30 mL)
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe solid residue was triturated with Et2O
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated in vacuo
  12. custompurified via flash column chromatography (2.5-5% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-4b1004a684d541d989077eab0c1c144c
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08575177B2

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