Dimethylacetamide → 2,3-dihydro-1H-indole-4-carbonitrile

HRID 1524305

반응식

HRID 1524305 반응식
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][NH:6]2.C[C:12]([N:14](C)C)=O>[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:2]([C:12]#[N:14])[C:3]=2[CH2:4][CH2:5]1

참가 물질

5

반응물 2

HCID 31374DimethylacetamideHCID 130983864-Bromo-2,3-dihydro-1H-indole

생성물 1

HCID 162444432,3-dihydro-1H-indole-4-carbonitrile

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매

실험 절차

Degas a solution of 4-bromo-2,3-dihydro-1H-indole (250 mg, 1.224 mmol) in DMAC (2 mL) under Ar. To this add zinc cyanide (147 mg, 1.224 mmol) followed by tetrakis-(triphenylphosphine) palladium(0) (143 mg, 0.123 mmol) and heat the reaction under argon in a sealed tube at 100° C. for 4 h. Quench the cooled reaction with sat. NH4Cl (50 mL) and extract with EtOAc (3×50 mL). Wash the organics with water (50 mL), dry (Na2SO4), then concentrate in vacuo to give a gum. Purify by silica gel chromatography eluting with 5% to 30% EtOAc/hexane. Pool and concentrate fractions containing product then dissolve the residue in Et2O (5 mL) and hexane (50 mL). Reconcentrate this to a solid. Suspend in hexane and filter washing with hexane to afford 2,3-dihydro-1H-indole-4-carbonitrile as a powder (131 mg). MS, electrospray 145.2 (M+H), rt 1.02 min.

후처리

  1. temperatureheat
  2. customthe reaction under argon in a sealed tube at 100° C. for 4 h
  3. customQuench
  4. customthe cooled reaction with sat. NH4Cl (50 mL)
  5. extractionextract with EtOAc (3×50 mL)
  6. washWash the organics with water (50 mL)
  7. dry with materialdry (Na2SO4)
  8. concentrationconcentrate in vacuo
  9. customto give a gum
  10. customPurify by silica gel chromatography
  11. washeluting with 5% to 30% EtOAc/hexane
  12. concentrationPool and concentrate fractions
  13. additioncontaining product
  14. dissolutionthen dissolve the residue in Et2O (5 mL)
  15. filtrationfilter
  16. washwashing with hexane

출처 및 근거

ORD 기록
ord-b972467f3d284df597192a5ba58e3693
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079880B2

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