Реакция #45321

Уравнение реакции

EtOAc hexane

methyl [(4-amino-5′-isopropyl-2′-methoxybiphenyl-2-yl)methyl][3,5-bis(trifluoromethyl)benzyl]carbamate

n-amyl nitrite

iodine

→

title compound

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

Растворители

methylene chloride

chloroform

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was heated to and
2. 2
   Температураmaintained
3. 3
   Температураat reflux for 2 h
4. 4
   Другоеcompletion of the reaction
5. 5
   Промывкаwashed with saturated sodium thiosulfate solution, brine
6. 6
   СушкаThe light yellow solution was dried over sodium sulfate

Методика

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).

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