Styrene → (2-Methoxy-benzyl)-[5-((E)-styryl)-quinolin-2-yl]-amine

HRID 1170072ノート

反応式

HRID 1170072 の反応式
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])=[N:7]2.[CH2:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][C:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2/[CH:22]=[CH:23]/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:7]=1

参加物

8

反応物 4

HCID 7501StyreneHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 67334552(5-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine

生成物 1

HCID 68433914(2-Methoxy-benzyl)-[5-((E)-styryl)-quinolin-2-yl]-amine

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

(5-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine (200 mg, 0.583 mmol) was dissolved in 3 mL dimethylformamide. Styrene (79 mg, 0.760 mmol), triethylamine (77 mg, 0.760 mmol), tri-o-tolylphosphine (14 mg, 0.046 mmol) and palladium(II)acetate (5 mg, 0.022 mmol) were added. The reaction mixture was stirred in a sealed tube at 100° C. for 2 h. The reaction mixture was poured into 30 mL water and extracted three times with ethyl acetate (30 mL each). The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient). The title compound was obtained as a light yellow solid (142 mg, 67%),

後処理

  1. extractionextracted three times with ethyl acetate (30 mL each)
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient)

出典と根拠

ORDレコード
ord-35e7f1c343af4c4b80203ffb32c8ed19
出典データセット
uspto-grants-2010_11
特許番号
US07825253B2

反応ノート

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