N-methyl-2-pyrrolidone → 2-Methyl-1H-indole-4-carbonitrile

HRID 475114노트

반응식

HRID 475114 반응식
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:11])[NH:6]2.[CH3:12][N:13]1C(=O)CCC1>[C-]#N.[C-]#N.[Zn+2].[Zn].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:11][C:5]1[NH:6][C:7]2[CH:8]=[CH:9][CH:10]=[C:2]([C:12]#[N:13])[C:3]=2[CH:4]=1

참가 물질

7

반응물 2

HCID 13387N-methyl-2-pyrrolidoneHCID 218145664-Bromo-2-methyl-1H-indole

생성물 1

HCID 695458182-Methyl-1H-indole-4-carbonitrile수율 96%

시약·촉매·용매 4

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 23994Zinc촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매

반응 조건

온도
120 °C

실험 절차

A mixture of 4-bromo-2-methyl-1H-indole (572 mg, 2.72 mmol), Zn(CN)2 (351 mg, 3.0 mmol), Zn (35 mg, 0.54 mmol), dppf (606 mg, 1.09 mmol), and Pd2(dba)3 (498 mg, 0.54 mmol) in NMP (10 mL) under argon atmosphere was heated at 120° C. for 18 h. After cooling to RT, the reaction mixture was partitioned between EtOAc (300 mL) and water (50 mL). The organic layer was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (3:1) to afford 2-methyl-1H-indole-4-carbonitrile as a yellow oil (408 mg, 96%). MS (ESI): m/z=157.2 [M+1]+.

후처리

  1. temperatureAfter cooling to RT
  2. customthe reaction mixture was partitioned between EtOAc (300 mL) and water (50 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by SiO2 chromatography
  8. washeluting with petroleum ether/EtOAc (3:1)

출처 및 근거

ORD 기록
ord-6e3d0cb2a7324c2ba74ccd588c588a64
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637537B2

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