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

HRID 348971

반응식

HRID 348971 반응식
[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]

참가 물질

4

반응물 2

HCID 21086136Methyl 1-butyl-4-iodo-1H-indole-6-carboxylateHCID 178418546HCID 178418546, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
150 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ee21cadc60b044f99f29ecd9e72965a7
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176242B2

연결된 노트

불러오는 중…