Dimethylformamide → Allyl-{5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pentyl}-methyl-amine

HRID 1633641ノート

反応式

HRID 1633641 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]OS(C)(=O)=O)=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.[CH2:27]([CH2:30][NH2:31])[CH:28]=C.[CH3:32]N(C=O)C>>[CH2:30]([N:31]([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:9]=[CH:10]2)[CH3:32])[CH:27]=[CH2:28]

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 4437323-Buten-1-amineHCID 86585585Methanesulfonic acid 5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pentyl ester

生成物 1

HCID 18679496Allyl-{5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pentyl}-methyl-amine収率 98%

実験手順

130 mg (0.26 mmol) Methanesulfonic acid 5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pentyl ester and 0.5 ml (5.2 mmol) N-allylmethylamine in 0.5 ml DMF were stirred at 60° C. for 2 h. The solution was concentrated and dissolved in water and CH2Cl2. 2M NaOH was added and the inorganic phase was extracted with CH2Cl2. The combined organic phases were washed with water and dried over Na2SO4. Column chromatography with CH2Cl2/MeOH 19:1 yielded 90 mg (98%) Allyl-{5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pentyl}-methyl-amine as orange oil, MS: 351(MH+).

後処理

  1. concentrationThe solution was concentrated
  2. dissolutiondissolved in water
  3. addition2M NaOH was added
  4. extractionthe inorganic phase was extracted with CH2Cl2
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over Na2SO4

出典と根拠

ORDレコード
ord-1a2b5dfffb874cdf884c66a67247e2e5
出典データセット
uspto-grants-2003_01
特許番号
US06503907B2

反応ノート

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