Nitrogen → N-[4-({4-[(dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)phenyl]-4-methyl-3-[(trimethylsilyl)ethynyl]benzamide

HRID 1527885ノート

反応式

HRID 1527885 の反応式
[CH3:1][P:2]([CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:29])[C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[C:23](I)[CH:22]=3)=[CH:15][C:14]=2[C:30]([F:33])([F:32])[F:31])[CH2:8][CH2:7]1)([CH3:4])=[O:3].N#N.C(N(CC)C(C)C)(C)C.[CH3:45][Si:46]([C:49]#[CH:50])([CH3:48])[CH3:47]>[Cu]I.CCOC(C)=O.O.CN(C=O)C>[CH3:1][P:2]([CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:29])[C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([C:50]#[C:49][Si:46]([CH3:48])([CH3:47])[CH3:45])[CH:22]=3)=[CH:15][C:14]=2[C:30]([F:33])([F:32])[F:31])[CH2:8][CH2:7]1)([CH3:4])=[O:3]

参加物

9

反応物 4

HCID 947NitrogenHCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 68911921N-[4-({4-[(dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)phenyl]-3-iodo-4-methylbenzamide

生成物 1

HCID 68911889N-[4-({4-[(dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)phenyl]-4-methyl-3-[(trimethylsilyl)ethynyl]benzamide

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

N-[4-({4-[(dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)phenyl]-3-iodo-4-methylbenzamide (5 mmol), Pd[(PPh3)]4 (289 mg, 0.25 mmol), CuI (71 mg, 0.375 mmol) is placed in a schlenk flask. The flask is subjected to 3 cycles of vacuum-refilling with N2. To this mixture is added anhydrous N,N-diisopropylethylamine (1.1 mL, 6 mmol), DMF (5 mL), and trimethylsilylacetylene (0.92 mL, 6.5 mmol). This solution is stirred at rt for 24 h. Water and EtOAc are added to the reaction mixture to facilitate the extraction. The combined organic layers are dried over Na2SO4, filtered, and then concentrated on a rotavap and the crude product is purified on a silica gel column (eluent: 5% MeOH in CH2Cl2, MeON is pre-saturated with ammonia gas).

後処理

  1. extractionthe extraction
  2. dry with materialThe combined organic layers are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated on a rotavap
  5. customthe crude product is purified on a silica gel column (eluent: 5% MeOH in CH2Cl2, MeON is pre-saturated with ammonia gas)

出典と根拠

ORDレコード
ord-3df43deea04240a399e6c0476dbef169
出典データセット
uspto-grants-2015_07
特許番号
US09090561B2

反応ノート

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