Nitrogen → 3-trimethylsilylethynyl-4-methyl-N-[4-((4-methylpiperazin-1-yl)methyl)-3-trifluoromethylphenyl]benzamide

HRID 2059787ノート

反応式

HRID 2059787 の反応式
I[C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)=[C:10]([C:22]([F:25])([F:24])[F:23])[CH:9]=1)=[O:6].N#N.C(N(CC)C(C)C)(C)C.[CH3:41][Si:42]([C:45]#[CH:46])([CH3:44])[CH3:43]>[Cu]I.CCOC(C)=O.O.CN(C=O)C>[CH3:29][C:28]1[CH:27]=[CH:26][C:4]([C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][N:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)=[C:10]([C:22]([F:23])([F:25])[F:24])[CH:9]=2)=[O:6])=[CH:3][C:2]=1[C:46]#[C:45][Si:42]([CH3:44])([CH3:43])[CH3:41]

参加物

9

反応物 4

HCID 947NitrogenHCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 468389103-iodo-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide

生成物 1

HCID 689162413-trimethylsilylethynyl-4-methyl-N-[4-((4-methylpiperazin-1-yl)methyl)-3-trifluoromethylphenyl]benzamide収率 82%

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

3-iodo-4-methyl-N-[4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]-benzamide (2.59 g, 5 mmol), Pd[(PPh3)]4 (289 mg, 0.25 mmol), CuI (71 mg, 0.375 mmol) was placed in a schlenk flask. The flask was subjected to 3 cycles of vacuum-refilling with N2. To this mixture was added anhydrous N,N-diisopropylethylamine (1.1 mL, 6 mmol), DMF (5 mL), and trimethylsilylacetylene (0.92 mL, 6.5 mmol). This solution was stirred at rt for 24 h. Water and EtOAc were added to the reaction mixture to facilitate the extraction. The combined organic layers were dried over Na2SO4, filtered, and then concentrated on a rotavap and the residue was purified on a silica gel column (eluent: 5% MeOH in CH2Cl2, MeOH was pre-saturated with ammonia gas) to give the desired product as a light yellow solid in 82% yield (2.0 g).

後処理

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

出典と根拠

ORDレコード
ord-005e737868844f4389f1bbb475e97e64
出典データセット
uspto-grants-2012_10
特許番号
US08278307B2

反応ノート

読み込み中…