Iodine → Methyl [3,5-bis(trifluoromethyl)benzyl][(4-iodo-5'-isopropyl-2'-methoxybiphenyl-2-yl)methyl]carbamate

HRID 217487

Reaktionsgleichung

Reaktionsgleichung von HRID 217487
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH:14]([CH3:16])[CH3:15])[CH:11]=[CH:10][C:9]=2[O:17][CH3:18])=[C:4]([CH2:19][N:20]([CH2:25][C:26]2[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=2)[C:21](=[O:24])[O:22][CH3:23])[CH:3]=1.CCCCCON=O.[I:48]I.CCOC(C)=O.CCCCCC>C(Cl)(Cl)Cl.C(Cl)Cl>[F:38][C:36]([F:39])([F:37])[C:28]1[CH:27]=[C:26]([CH:31]=[C:30]([C:32]([F:34])([F:33])[F:35])[CH:29]=1)[CH2:25][N:20]([CH2:19][C:4]1[CH:3]=[C:2]([I:48])[CH:7]=[CH:6][C:5]=1[C:8]1[CH:13]=[C:12]([CH:14]([CH3:15])[CH3:16])[CH:11]=[CH:10][C:9]=1[O:17][CH3:18])[C:21](=[O:24])[O:22][CH3:23]

Komponenten

7

Edukt 4

HCID 807IodineHCID 10026Pentyl nitriteHCID 11678430Methyl [(4-amino-5'-isopropyl-2'-methoxybiphenyl-2-yl)methyl][3,5-bis(trifluoromethyl)benzyl]carbamateHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 11527580Methyl [3,5-bis(trifluoromethyl)benzyl][(4-iodo-5'-isopropyl-2'-methoxybiphenyl-2-yl)methyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of the methyl [(4-amino-5′-isopropyl-2′-methoxybiphenyl-2-yl)methyl][3,5-bis(trifluoromethyl)benzyl]carbamate from Example 9 (0.31 g, 0.56 mmol) in chloroform (10 ml), n-amyl nitrite (0.11 ml, 0.84 mmol) and iodine (0.28 g, 1.1 mmol) were added. The mixture was heated to and maintained at reflux for 2 h. TLC analysis (5:95 EtOAc/hexane) showed completion of the reaction. The mixture was diluted with methylene chloride (20 ml) and washed with saturated sodium thiosulfate solution, brine. The light yellow solution was dried over sodium sulfate. The title compound was obtained by flash column chromatography using 5:95 EtOAc/hexane as the eluant. 1H NMR (CDCl3, 500 MHz) δ 7.74 (s, 1H), 7.67 (dd, J=8.0, 2.0 Hz, 1H), 7.47 (m, 1H), 7.31 (dd, J=8.0, 2.0 Hz, 1H), 7.21 (d, J=8.0 Hz, 1H), 7.16 (d, J=8.5 Hz, 1H), 6.95 (d, J=8.0 Hz, 1H), 6.91 (dd, J=4.0, 2.5 Hz, 1H), 6.87 (d, J=8.5 Hz, 1), 4.20-4.48 (m, 4H), 3.78 (s, 3H), 3.70 (s, 3H), 2.92 (m, 1H), 1.23 (s, 3H), 1.21 (s, 3H), LC-MS (M+1) 666.0 (4.74 min).

Aufarbeitung

  1. temperatureThe mixture was heated to and
  2. temperaturemaintained
  3. temperatureat reflux for 2 h
  4. customcompletion of the reaction
  5. washwashed with saturated sodium thiosulfate solution, brine
  6. dry with materialThe light yellow solution was dried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-f9925f8a99b84d8aa7c11be6b749ff33
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193365B2

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