PyBOP → 5-(3-Chloro-4-isopropoxyphenyl)-3-(1H-indol-5-yl)-1,2,4-oxadiazole

HRID 423292

Reaktionsgleichung

Reaktionsgleichung von HRID 423292
[OH:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2)=[NH:4].[Cl:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[O:24][CH:25]([CH3:27])[CH3:26])[C:18](O)=O.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:14][C:15]1[CH:16]=[C:17]([C:18]2[O:1][N:2]=[C:3]([C:5]3[CH:6]=[C:7]4[C:11](=[CH:12][CH:13]=3)[NH:10][CH:9]=[CH:8]4)[N:4]=2)[CH:21]=[CH:22][C:23]=1[O:24][CH:25]([CH3:26])[CH3:27]

Komponenten

5

Edukt 3

HCID 2724699PyBOPHCID 225977283-Chloro-4-(propan-2-yloxy)benzoic acidHCID 178513238HCID 178513238, Verbindung

Produkt 1

HCID 593183535-(3-Chloro-4-isopropoxyphenyl)-3-(1H-indol-5-yl)-1,2,4-oxadiazoleAusbeute 11,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

D1 (500 mg), D4 (611 mg) and PyBOP (1.66 g) were dissolved in DMF and stirred overnight. The reaction mixture was then evaporated and partitioned between EtOAc and H2O. The organic layer was washed with H2O (×2) then brine, dried over MgSO4, filtered and evaporated to give the crude product. This was purified on a silica cartridge, eluting with a 0 to 50% mixture of Et2O in hexane to give the title compound (120 mg) as a white solid. δH (CDCl3, 400 MHz): 1.43 (6H, d), 4.69 (1H, septet), 6.92 (1H, s), 7.04 (1H, d), 7.25 (1H, s), 7.48 (1H, d), 8.00 (1H, d), 8.07 (1H, d), 8.25 (1H, s), 8.39 (1H, br. s), 8.50 (1H, s). MS (ES): C19H16ClN3O2 requires 353; found 354 (MH+).

Aufarbeitung

  1. customThe reaction mixture was then evaporated
  2. custompartitioned between EtOAc and H2O
  3. washThe organic layer was washed with H2O (×2)
  4. dry with materialbrine, dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude product
  8. customThis was purified on a silica cartridge
  9. washeluting with a 0 to 50% mixture of Et2O in hexane

Quellen und Nachweise

ORD-Eintrag
ord-4f7805d80bb0444b915b9cd35f8d77b5
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101775B2

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