Iodoform → 1,1-Dimethylethyl 7-[(2-fluoro-4-Iodophenyl)oxy]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

HRID 222766

Reaktionsgleichung

Reaktionsgleichung von HRID 222766
N[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:26]=[CH:25][C:12]3[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17][C:11]=3[CH:10]=2)=[C:4]([F:27])[CH:3]=1.C(I)(I)[I:29].N(OC(C)(C)C)=O>O1CCCC1>[F:27][C:4]1[CH:3]=[C:2]([I:29])[CH:7]=[CH:6][C:5]=1[O:8][C:9]1[CH:26]=[CH:25][C:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17][C:11]=2[CH:10]=1

Komponenten

5

Edukt 3

HCID 6374IodoformHCID 10906Tert-Butyl nitriteHCID 589845681,1-Dimethylethyl 7-[(4-amino-2-fluorophenyl)oxy]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Produkt 1

HCID 589845721,1-Dimethylethyl 7-[(2-fluoro-4-Iodophenyl)oxy]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1,1-dimethylethyl 7-[(4-amino-2-fluorophenyl)oxy]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (E274, Step 2) (0.5 g, 1.34 mmol) and iodoform (1 g, 2.69 mmol) in tetrahydrofuran (10 ml) was added dropwise tert-butyl nitrite (0.32 ml, 2.69 mmol). The reaction was then heated at reflux for 1 hour, cooled and concentrated in vacuo and resulting residue was purified by column chromatography eluting with a mixture of ethyl acetate:pentane (1:10) to afford the title compound. MS (ES+) m/e 384 [M-COOtBu]+.

Aufarbeitung

  1. temperatureThe reaction was then heated
  2. temperatureat reflux for 1 hour
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customresulting residue
  6. customwas purified by column chromatography
  7. washeluting with a mixture of ethyl acetate:pentane (1:10)

Quellen und Nachweise

ORD-Eintrag
ord-58f1c6135a8b4fa39a18c13a6597f3f0
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207331B2

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