N-methyl-2-pyrrolidone → HCID 58403540, 화합물

HRID 475267노트

반응식

HRID 475267 반응식
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH3:11])=[CH:5][NH:6]2.[CH3:12][N:13]1C(=O)CCC1>[C-]#N.[C-]#N.[Zn+2].[Zn].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].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]>[CH3:11][C:4]1[C:3]2[C:2]([C:12]#[N:13])=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6][CH:5]=1

참가 물질

7

반응물 2

HCID 13387N-methyl-2-pyrrolidoneHCID 529877044-Bromo-3-methyl-1H-indole

생성물 1

HCID 58403540HCID 58403540, 화합물수율 59%

시약·촉매·용매 4

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

반응 조건

온도
140 °C

실험 절차

To a solution of 230 (454 mg, 2.16 mmol) in NMP (4.5 mL) under argon atmosphere was added Zn(CN)2 (252 mg, 2.16 mmol), zinc powder (27 mg, 0.43 mmol), Pd2(dba)3 (0) (293 mg, 0.32 mmol), and dppf (358 mg, 0.65 mmol). The solution was heated at 140° C. for 18 h, the mixture was cooled and partitioned between EtOAc (100 mL) and H2O (30 mL). The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated to dryness in vacuo. The residue was purified by SiO2 chromatography eluting with 10% EtOAc/petroleum ether to afford 200 mg (59%) of 3-methyl-1H-indole-4-carbonitrile (232) as white solid: MS (ESI) m/z=157.1 [M+1]+.

후처리

  1. temperaturethe mixture was cooled
  2. custompartitioned between EtOAc (100 mL) and H2O (30 mL)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness in vacuo
  8. customThe residue was purified by SiO2 chromatography
  9. washeluting with 10% EtOAc/petroleum ether

출처 및 근거

ORD 기록
ord-95a18e6ebff34a0c94968929095ef21b
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637537B2

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