Methyl 1-butyl-4-iodo-1H-indole-6-carboxylate → Methyl 1-butyl-4-cyano-1H-indole-6-carboxylate

HRID 14180

反応式

HRID 14180 の反応式
[CH2:1]([N:5]1[C:13]2[C:8](=[C:9](I)[CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4].[Cu][C:20]#[N:21]>CN1C(=O)CCC1>[CH2:1]([N:5]1[C:13]2[C:8](=[C:9]([C:20]#[N:21])[CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4]

参加物

4

反応物 2

HCID 21086136Methyl 1-butyl-4-iodo-1H-indole-6-carboxylateHCID 178418546HCID 178418546、化合物

生成物 1

HCID 21086135Methyl 1-butyl-4-cyano-1H-indole-6-carboxylate収率 47.4%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
150 °C

実験手順

To a mixture of methyl 1-butyl-4-iodo-1H-indole-6-carboxylate (Example SP-218, Step 4) (1.47 g) in N-methyl pyrrolidinone (15 mL) was added copper (I) cyanide (1.1 g). The mixture was heated to 150° C. for 6 h, removed from heat and cooled to room temperature. The mixture was partitioned between water and ethyl acetate and the layers were separated. The organic layer was washed three times with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (100 mL) using 20% ethyl acetate as eluent to give 0.5 g of the title compound: 1H NMR (CDCl3) δ 0.955, 1.32, 1.85, 3.98, 4.23, 6.76, 7.43, 8.16, 8.30.

後処理

  1. customremoved
  2. temperaturefrom heat
  3. temperaturecooled to room temperature
  4. customThe mixture was partitioned between water and ethyl acetate
  5. customthe layers were separated
  6. washThe organic layer was washed three times with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-508a6e30e6544766b9749c4d8ed0c4c4
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

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