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2-Bromo-6-fluoropyridine → 2-{6-[(6-Bromopyridin-2-yl)oxy]-2,3-dihydro-4h-1,4-benzoxazin-4-yl}-6,6-dimethyl-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

HRID 885985
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 885985
[CH3:1][C:2]1([CH3:23])[NH:7][C:6](=[O:8])[C:5]2[S:9][C:10]([N:12]3[C:17]4[CH:18]=[C:19]([OH:22])[CH:20]=[CH:21][C:16]=4[O:15][CH2:14][CH2:13]3)=[N:11][C:4]=2[CH2:3]1.[Br:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27](F)[N:26]=1.CC(C)([O-])C.[Na+]>C1COCC1>[Br:24][C:25]1[N:26]=[C:27]([O:22][C:19]2[CH:20]=[CH:21][C:16]3[O:15][CH2:14][CH2:13][N:12]([C:10]4[S:9][C:5]5[C:6](=[O:8])[NH:7][C:2]([CH3:23])([CH3:1])[CH2:3][C:4]=5[N:11]=4)[C:17]=3[CH:18]=2)[CH:28]=[CH:29][CH:30]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6394382-Bromo-6-fluoropyridineHCID 23676156Sodium t-butoxideHCID 671855836,6-Dimethyl-2-(6-hydroxy-2,3-dihydrobenzo[1,4]oxazin-4-yl)-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

Produkt 1

HCID 873022572-{6-[(6-Bromopyridin-2-yl)oxy]-2,3-dihydro-4h-1,4-benzoxazin-4-yl}-6,6-dimethyl-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-oneAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a solution of Example 57 (50 mg, 0.151 mmol) in THF (4 mL) was added 2-bromo-6-fluoropyridine (53 mg, 0.302 mmol) and sodium tert-butoxide (58 mg, 0.604 mmol). The mixture was heated to 150° C. under microwave irradiation for 30 minutes then cooled to r.t. The resulting mixture was partitioned between DCM (50 mL) and water (50 mL); the organic phase was washed with brine (50 mL), dried (MgSO4), and concentrated in vacuo. The residue was triturated with Et2O to yield the title compound (10 mg, 14%) as an off-white solid. δH (CDCl3) 7.95 (1H, d, J 2.6 Hz), 7.52 (1H, t, J 7.9 Hz), 7.19 (1H, d, J 7.5 Hz), 6.97 (1H, d, J 8.9 Hz), 6.85 (1H, dd, J 8.9 and 2.6 Hz), 6.80 (1H, d, J 8.1 Hz), 5.32 (1H, s), 4.39-4.32 (2H, m), 4.16-4.10 (2H, m), 2.86 (2H, s), 1.38 (6H, s). LCMS (ES+) 487.0 (M+H)+, RT 3.73 minutes (Method 1).

Aufarbeitung

  1. temperaturethen cooled to r.t
  2. customThe resulting mixture was partitioned between DCM (50 mL) and water (50 mL)
  3. washthe organic phase was washed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-24b224c4bff047abb226adc0538dce2f
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08242116B2

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