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

HRID 17043

반응식

HRID 17043 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-26af4ad9262e4124a7b8babb8ddb9ef0
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737295B2

연결된 노트

불러오는 중…