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Sodium Carbonate → (S)-methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(2'-(but-3-en-1-yl)-[1,1'-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

HRID 1400727
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1400727
[CH2:1]([O:4][C:5]1([CH3:38])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22](Br)[CH:21]=4)[CH:19]=[C:15]3[N:14]=[C:13]([CH3:27])[C:12]=2[C@H:28]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:29]([O:31][CH3:32])=[O:30])[CH2:7][CH2:6]1)[CH:2]=[CH2:3].[CH2:39]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1B1OC(=O)CN(C)CC(=O)O1)[CH2:40][CH:41]=[CH2:42].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.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>[CH2:1]([O:4][C:5]1([CH3:38])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([C:20]4[CH:21]=[C:22]([C:44]5[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=5[CH2:39][CH2:40][CH:41]=[CH2:42])[CH:23]=[CH:24][CH:25]=4)[CH:19]=[C:15]3[N:14]=[C:13]([CH3:27])[C:12]=2[C@H:28]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:29]([O:31][CH3:32])=[O:30])[CH2:7][CH2:6]1)[CH:2]=[CH2:3]
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Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 86710779(S)-methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetateHCID 867107802-(2-(But-3-en-1-yl)phenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

Produkt 1

HCID 86710778(S)-methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(2'-(but-3-en-1-yl)-[1,1'-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate
Ausbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of (S)-methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (250 mg, 0.427 mmol) in DMF (5 mL) was added 2-(2-(but-3-en-1-yl)phenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione (147 mg, 0.512 mmol), 2M sodium carbonate (0.427 mL, 0.854 mmol), and tetrakis(triphenylphosphine)palladium(0)(35 mg, 0.030 mmol). This reaction mixture was flushed with N2 and heated at 90° C. for 24 h. Upon completion of the reaction, the reaction mixture was partitioned between EtOAc and water. The organic phase was washed with water (3×), dried (MgSO4), filtered, and concentrated in vacuo to give the crude product as a brown oil. This was purified by Biotage chromatography (0-40% EtOAc/hexanes) to give 233 mg (86% yield) of (S)-methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(2′-(but-3-en-1-yl)-[1,1′-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate as a colorless oil. LCMS (M+H).=637.

Aufarbeitung

  1. customThis reaction mixture was flushed with N2
  2. customUpon completion of the reaction
  3. customthe reaction mixture was partitioned between EtOAc and water
  4. washThe organic phase was washed with water (3×)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the crude product as a brown oil
  9. customThis was purified by Biotage chromatography (0-40% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9deca7ccac894aa7a02497cad34b7d28
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08906929B2

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