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Nitrogen → (2S)-Methyl 2-(7-(4-allylchroman-6-yl)-2-(3-bromophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

HRID 1400712
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1400712
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:28]=[C:11]3[N:12]=[C:13]([CH3:27])[C:14]([C@H:17]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:18]([O:20][CH3:21])=[O:19])=[C:15](I)[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:29]([CH:32]1[C:41]2[C:36](=[CH:37][CH:38]=[C:39](B3OC(C)(C)C(C)(C)O3)[CH:40]=2)[O:35][CH2:34][CH2:33]1)[CH:30]=[CH2:31].C([O-])([O-])=O.[Na+].[Na+].N#N>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>[CH2:29]([CH:32]1[C:41]2[C:36](=[CH:37][CH:38]=[C:39]([C:15]3[N:10]4[N:9]=[C:8]([C:4]5[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=5)[CH:28]=[C:11]4[N:12]=[C:13]([CH3:27])[C:14]=3[C@H:17]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:18]([O:20][CH3:21])=[O:19])[CH:40]=2)[O:35][CH2:34][CH2:33]1)[CH:30]=[CH2:31]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 86710746(S)-methyl 2-(2-(3-bromophenyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetateHCID 867107632-(4-Allylchroman-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 86710765
(2S)-Methyl 2-(7-(4-allylchroman-6-yl)-2-(3-bromophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate
Ausbeute 190,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of (S)-methyl 2-(2-(3-bromophenyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.375 g, 0.374 mmol), 2-(4-allylchroman-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.123 g, 0.411 mmol) and 2.0 M Na2CO3 (0.374 ml, 0.747 mmol) in DMF (3.74 ml) was sparged with N2 for 10 min, treated with Pd(Ph3P)4 (0.030 g, 0.026 mmol), sparged for 5 minutes, then heated (90° C.) for 16 h. The reaction was cooled, diluted with water (20 mL) and extracted with EtOAc. The organic layer was dried (MgSO4), filtered, and concentrated and the residue was purified by biotage (40 g SiO2, 0% (3 CV), 0-40% (15 CV), 60% (2 CV), EtOAc in hexanes). Fractions containing desired product combined, concentrated and re-purified (40 g SiO2, 0% (3 CV), 0-60% (15 CV), 60% (2 CV), EtOAc in hexanes) to afford the desired product (0.431 g, 0.713 mmol, 44.6% yield). LCMS (M+H)=606.4.

Aufarbeitung

  1. customsparged for 5 minutes
  2. temperatureThe reaction was cooled
  3. additiondiluted with water (20 mL)
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue was purified by biotage (40 g SiO2, 0% (3 CV), 0-40% (15 CV), 60% (2 CV), EtOAc in hexanes)
  9. additionFractions containing desired product
  10. concentrationconcentrated
  11. customre-purified (40 g SiO2, 0% (3 CV), 0-60% (15 CV), 60% (2 CV), EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2ca9e898352e4897a18360a891527b1e
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08906929B2

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