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Dimethylformamide → (S)-Methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(5'-fluoro-2'-hydroxy-[1,1'-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

HRID 1400741
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1400741
[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].[F:39][C:40]1[CH:41]=[CH:42][C:43]([OH:49])=[C:44](B(O)O)[CH:45]=1.CN(C=O)C.C([O-])([O-])=O.[Na+].[Na+]>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>[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:42]5[CH:41]=[C:40]([F:39])[CH:45]=[CH:44][C:43]=5[OH:49])[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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 37724765-Fluoro-2-hydroxyphenylboronic acidHCID 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)acetate

Produkt 1

HCID 86710797
(S)-Methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(5'-fluoro-2'-hydroxy-[1,1'-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate
Ausbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To (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 (0.24 g, 0.41 mmol, 1 equiv), (5-fluoro-2-hydroxyphenyl)boronic acid (96 mg, 0.62 mmol, 1.5 equiv), and Pd(PPh3)4 (47 mg, 0.041 mmol, 0.1 equiv) was added DMF (4.1 mL that had been degassed by sparging with nitrogen for 10 min) Na2CO3 (0.41 mL of a 2 M aqueous solution, 0.82 mmol, 2 equiv) was added and the reaction was heated to 90° C. for 3 h. Upon cooling to ambient temperature, the reaction was diluted with EtOAc and washed with water. The EtOAc layer was dried (Na2SO4) and concentrated in vacuo. The crude product was purified by flash column chromatography (0-60% acetone in hexane) to provide the product as a yellow foam (0.19 g, 75%). 1H NMR (400 MHz, CDCl3) δ 8.13-8.08 (m, 1H), 8.05-8.00 (m, 1H), 7.67-7.48 (m, 3H), 7.09-6.94 (m, 4H), 6.07-5.92 (m, 1H), 5.45-5.36 (m, 1H), 5.22-5.07 (m, 2H), 4.04-3.97 (m, 2H), 3.81-3.77 (m, 3H), 3.77-3.74 (m, 4H), 2.74-2.65 (m, 3H), 2.08-1.94 (m, 3H), 1.80-1.68 (m, 1H), 1.36 (s, 3H), 1.24 (s, 9H). LCMS (M+1)=617.35.

Aufarbeitung

  1. additionwas added
  2. temperatureUpon cooling to ambient temperature
  3. washwashed with water
  4. dry with materialThe EtOAc layer was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography (0-60% acetone in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-797f7f59ca9d486781ce794bc68ea62a
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08906929B2

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