Diisopropylethylamine → Ethyl [2-methyl-4-({pentyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetate

HRID 1269608ノート

反応式

HRID 1269608 の反応式
[CH2:1]([NH:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH3:5].Br[CH2:24][C:25]1[CH:37]=[CH:36][C:28]([O:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:27]([CH3:38])[CH:26]=1.C(N(CC)C(C)C)(C)C>CC#N>[CH3:38][C:27]1[CH:26]=[C:25]([CH2:24][N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:7]2[CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][CH:14]=3)[CH:10]=[CH:11][CH:12]=2)[CH:37]=[CH:36][C:28]=1[O:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 18448425N-Pentyl-N-[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amineHCID 58622841Ethyl [4-(bromomethyl)-2-methylphenoxy]acetate

生成物 1

HCID 58622867Ethyl [2-methyl-4-({pentyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetate収率 55.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of N-pentyl-N-[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amine (70 mg, 0.23 mmol) in anhydrous MeCN (6 mL) under nitrogen at room temperature, was added ethyl [4-(bromomethyl)-2-methylphenoxy]acetate (65.4 mg, 0.23 mmol) and N,N-diisopropyethylamine (39.6 μL, 0.23 mmol). The resultant solution was heated to reflux and stirred for 4 h. The reaction mixture was allowed to cool to room temperature and the solvent was removed in vacuo. The residue was partitioned between CHCl3 (20 mL) and water (10 mL). The organic solution was passed through a hydrophobic frit and the solvent was removed in vacuo. Purification by SPE (5 g Silica cartridge) eluted with 1:200–1:100 EtOAc:cyclohexane afforded the title compound as a colourless oil (66 mg).

後処理

  1. temperatureto reflux
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between CHCl3 (20 mL) and water (10 mL)
  4. customthe solvent was removed in vacuo
  5. customPurification by SPE (5 g Silica cartridge)
  6. washeluted with 1:200–1:100 EtOAc

出典と根拠

ORDレコード
ord-0268173e636146a290617cea0bd03154
出典データセット
uspto-grants-2007_04
特許番号
US07199239B2

反応ノート

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