N-methyl-2-pyrrolidone → HCID 58403540、化合物

HRID 475267ノート

反応式

HRID 475267 の反応式
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

参加物

7

反応物 2

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

生成物 1

HCID 58403540HCID 58403540、化合物収率 59%

試薬・触媒・溶媒 4

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

反応条件

温度
140 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-95a18e6ebff34a0c94968929095ef21b
出典データセット
uspto-grants-2014_01
特許番号
US08637537B2

反応ノート

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