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

HRID 217487

反応式

HRID 217487 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f9925f8a99b84d8aa7c11be6b749ff33
出典データセット
uspto-grants-2012_06
特許番号
US08193365B2

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