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

HRID 1019677노트

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HRID 1019677 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

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

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3d183a4f166c4e53a38539489b18c102
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716285B2

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