Potassium Carbonate → Methyl [3,5-bis(trifluoromethyl)benzyl][(5'-isopropyl-2'-methoxy-4-nitrobiphenyl-2-yl)methyl]carbamate

HRID 217485

反応式

HRID 217485 の反応式
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[CH2:6][N:7]([CH2:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=1Br)[C:8](=[O:11])[O:9][CH3:10].[CH3:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([CH:40]([CH3:42])[CH3:41])=[CH:36][C:35]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].CC(C)=O.O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(C)=O.CCCCCC>[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[CH2:6][N:7]([CH2:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=1[C:39]1[CH:38]=[C:37]([CH:40]([CH3:42])[CH3:41])[CH:36]=[CH:35][C:34]=1[O:33][CH3:32])[C:8](=[O:11])[O:9][CH3:10]

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 45891905-Isopropyl-2-methoxyphenylboronic acidHCID 18366337Propan-2-one--water (1/1)HCID 86615394Methyl [3,5-bis(trifluoromethyl)benzyl](2-bromo-5-nitrobenzyl)carbamate

生成物 1

HCID 11563293Methyl [3,5-bis(trifluoromethyl)benzyl][(5'-isopropyl-2'-methoxy-4-nitrobiphenyl-2-yl)methyl]carbamate

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 21880519Acetone hexane溶媒

実験手順

To a mixture of Methyl [3,5-bis(trifluoromethyl)benzyl](2-bromo-5-nitrobenzyl)carbamate from Step D (0.39 g, 0.75 mmol), 2-methoxy-5-isopropylphenyl boronic acid (0.175 g, 0.90 mmol), and potassium carbonate (0.21 g, 1.50 mmol) in 4:1 acetone/water (10 ml), a catalytic amount of palladium acetate (10 mg) was added. The mixture was heated to and maintained at reflux for 2 h. TLC analysis (acetone/hexane=5:95) showed completion of the reaction. The acetone was removed under reduced pressure and the organic was extracted with methylene chloride (3×25 ml). The combined organic layers were washed with brine and dried over sodium sulfate. The title compound was obtained by flash column chromatography using 5:95 acetone/hexane as the eluant. NMR (CDCl3, 500 MHz) δ 8.20 (m, 2H), 7.75 (s, 1H), 7.48 (M, 1H), 7.40 (d, J=8.0 Hz, 1H), 7.29 (m, 1H), 6.93 (m, 2H), 4.25-4.60 (m, 4H), 3.80 (m, 3H), 3.69 (s, 3H), 2.89 (m, 1H),1.20 (s, 6H). LC-MS (M+1) 585.4 (4.49 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. customThe acetone was removed under reduced pressure
  6. extractionthe organic was extracted with methylene chloride (3×25 ml)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over sodium sulfate

出典と根拠

ORDレコード
ord-585cc6b5c51644f89764685d60484495
出典データセット
uspto-grants-2012_06
特許番号
US08193365B2

関連ノート

読み込み中…