Dimethylformamide → tert-Butyl (6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)carbamate

HRID 1019677ノート

反応式

HRID 1019677 の反応式
[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=2)[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:20][N:21](C=O)C>[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>[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:20]#[N:21])[CH:15]=2)[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 6228DimethylformamideHCID 17758659tert-Butyl (6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)carbamate

生成物 1

HCID 66692977tert-Butyl (6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)carbamate収率 67%

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒

反応条件

温度
90 °C

実験手順

To an argon sparkled solution of XXIV (1 g, 3.04 mmol), and zinc cyanide (352 mg, 3 mmol) in DMF (5 mL) was added tetrakis-(triphenylphosphine) palladium (0) (300 mg, 0.228 mmol) and the reaction mixture was then heated at 90° C. overnight. When the mixture was cooled down and partitioned between EtOAc and water, the aqueous phase was separated and extracted with EtOAc. The combined organic phase was washed with saturated NaCl, dried over Na2SO4 and concentrated. The residue was purified by silica gel column to give (6-cyano-1,2,3,4-tetrahydro-quinolin-3-yl)-carbamic acid tert-butyl ester XXV (560 mg, 67%) as white solid.

後処理

  1. temperatureWhen the mixture was cooled down
  2. custompartitioned between EtOAc and water
  3. customthe aqueous phase was separated
  4. extractionextracted with EtOAc
  5. washThe combined organic phase was washed with saturated NaCl
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column

出典と根拠

ORDレコード
ord-3d183a4f166c4e53a38539489b18c102
出典データセット
uspto-grants-2014_05
特許番号
US08716285B2

反応ノート

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