Tetrahydrofuran → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylbut-3-enyl)-thiazolo[5,4-b]pyridine

HRID 1177424Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177424
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:16]=3)=[C:9]([F:29])[CH:8]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].O1C[CH2:43][CH2:42][CH2:41]1.C(I)C=C.[NH4+].[Cl-]>CN(C=O)C>[O:3]1[CH2:4][CH2:5][CH2:6][O:1][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17]([CH:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:43][CH:42]=[CH2:41])[N:16]=3)=[C:9]([F:29])[CH:8]=1

Komponenten

7

Edukt 5

HCID 8028TetrahydrofuranHCID 11166Allyl iodideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 591748722-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-benzylthiazolo[5,4-b]pyridine

Produkt 1

HCID 686357552-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylbut-3-enyl)-thiazolo[5,4-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a slurry of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-benzylthiazolo[5,4-b]pyridine (2.28 g, 5.6 mmol) in 40 mL DMF under argon was added lithium bis(trimethylsilyl)amide, 1.0 m solution in tetrahydrofuran (7.0 mL, 7.0 mmol). A very deep blue solution resulted. After 2 min, allyl iodide (0.77 mL, 8.4 mmol) was added via syringe and the reaction became brown. After 5 min, sat'd aq. NH4Cl was added and the reaction partitioned between water and EA. The organic was washed with water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting material was sonicated in MTBE, filtered, and dried to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylbut-3-enyl)thiazolo[5,4-b]pyridine as a yellow solid. MS (ESI) m/z: Calculated: 446.2; Observed: 447.1 (M++1).

Aufarbeitung

  1. customA very deep blue solution resulted
  2. waitAfter 5 min
  3. additionwas added
  4. customthe reaction partitioned between water and EA
  5. washThe organic was washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting material was sonicated in MTBE
  10. filtrationfiltered
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-32fbbe606ad4433d9cc4f10c0db43dee
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842685B2

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