Dimethylformamide → HCID 22335233, 화합물

HRID 586714노트

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HRID 586714 반응식
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13](Cl)[CH:12]=[CH:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Li+].[CH3:21][N:22](C)C=O>[C-]#N.[Zn+2].[C-]#N.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]>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13]([C:21]#[N:22])[CH:12]=[CH:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 433294Lithium ChlorideHCID 162287476-Benzyl-2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine

생성물 1

HCID 22335233HCID 22335233, 화합물

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매3회

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온도
100 °C

실험 절차

6-Benzyl-2-chloro-5,6,7,8-tetrahydro-[1,6]naphthyridine (129 mg, 0.5 mmol) (See Reference WO9830560 Example 33b) was added to zinc cyanide (58.7 mg, 0.5 mmol), lithium chloride (27 mg, 0.65 mmol) and tetrakis(triphenylphosphine)palladium (0) (35 mg, 0.03 mmol) in N,N-dimethylformamide (3 ml). The mixture was purged with argon and was heated at 100° C. for 17 hours. The reaction mixture was cooled to room temperature and a further quantity of tetrakis(triphenylphosphine)palladium (0) (35 mg, 0.03 mmol) was added and the mixture was heated at 125° C. for 3 hours. The reaction mixture was cooled to room temperature and a further quantity of tetrakis(triphenylphosphine)palladium (0) (35 mg, 0.03 mmol) was added and the mixture was heated at 125° C. for 3 hours. The reaction mixture was cooled to room temperature and was partitioned between ethyl acetate (40 ml) and water (40 ml). The phases were separated and the organic phase was washed with water (3×30 ml) dried over magnesium sulphate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel using ethyl acetate in pentane as eluant (33:67) to give the title compound as a brown gum (97 mg).

후처리

  1. customThe mixture was purged with argon
  2. temperatureThe reaction mixture was cooled to room temperature
  3. temperaturethe mixture was heated at 125° C. for 3 hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. temperaturethe mixture was heated at 125° C. for 3 hours
  6. temperatureThe reaction mixture was cooled to room temperature
  7. customwas partitioned between ethyl acetate (40 ml) and water (40 ml)
  8. customThe phases were separated
  9. washthe organic phase was washed with water (3×30 ml)
  10. dry with materialdried over magnesium sulphate
  11. customevaporated under reduced pressure
  12. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-2cab6c20059447128af231a092f394ae
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936619B2

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