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Potassium Hydroxide → (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[(2'-chloro-4-cyclopropyl-5'-isopropylbiphenyl-2-yl)methyl]-4-methyl-1,3-oxazolidin-2-one

HRID 1994642
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1994642
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24](Br)[CH:23]=[CH:22][C:21]=3[C:27]3[CH:32]=[C:31]([CH:33]([CH3:35])[CH3:34])[CH:30]=[CH:29][C:28]=3[Cl:36])[C@H:14]2[CH3:37])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH:40]1(B(O)O)[CH2:42][CH2:41]1.[OH-].[K+]>O1CCOCC1.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([CH:40]4[CH2:42][CH2:41]4)[CH:23]=[CH:22][C:21]=3[C:27]3[CH:32]=[C:31]([CH:33]([CH3:35])[CH3:34])[CH:30]=[CH:29][C:28]=3[Cl:36])[C@H:14]2[CH3:37])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 2760897Cyclopropylboronic acidHCID 11556418(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[(4-bromo-2'-chloro-5'-isopropylbiphenyl-2-yl)methyl]-4-methyl-1,3-oxazolidin-2-one

Produkt 1

HCID 11527223(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[(2'-chloro-4-cyclopropyl-5'-isopropylbiphenyl-2-yl)methyl]-4-methyl-1,3-oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[(4-bromo-2′-chloro-5′-isopropylbiphenyl-2-yl)methyl]-4-methyl-1,3-oxazolidin-2-one (27 mg, 0.043 mmol) in 1,4-dioxane (1 mL) was added cyclopropylboronic acid (9 mg, 0.10 mmol), [1,1′-bis(diphenylphosphino) ferrocene] dichloropalladium (II) (10.4 mg, 30 mol %) and aqueous potassium hydroxide (42 μL, 3M, 3 eq.). The reaction mixture was purged with nitrogen and then sealed in a microwave vessel. The reaction vessel was subject to microwave irradiation at 120° C. for 20 min. Crude mixture was worked up with water and EtOAc. The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give the crude product. This was purified by preparative TLC plate eluted by 20% EtOAc in hexanes to afford the titled compound. LC-MS: 595.99 (M+1)+. 1H NMR (CDCl3, 500 MHz) a 6:4 mixture of rotamers δ 7.82-7.86 (m, 1H), 7.66-7.72 (m, 2H), 7.36-7.40 (m, 1H), 7.21-7.23 (m, 0.5H), 7.11-7.19 (m, 3H), 7.01-7.08 (m, 1.5H), 5.58 (d, J=8.0 Hz, 0.4H), 5.50 (d, J=8.0 Hz, 0.6H), 4.88 (d, J=15.1 Hz, 0.6H), 4.71 (d, J=15.6 Hz, 0.4H), 3.76-3.95 (m, 2H), 2.84-2.95 (m, 1H), 1.92-2.00 (m, 1H), 1.18-1.29 (m, 6H), 1.00-1.07 (m, 2H), 0.71-0.82 (m, 2H), 0.47 (d, J=6.6 Hz, 1.2H), 0.42 (d, J=6.6 Hz, 1.8H).

Aufarbeitung

  1. customThe reaction mixture was purged with nitrogen
  2. customsealed in a microwave vessel
  3. customirradiation at 120° C. for 20 min
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customThis was purified by preparative TLC plate
  8. washeluted by 20% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ce3961a811bc4e8581ea115844d0e18a
Quelldatensatz
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07652049B2

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