Dimethylformamide → HCID 22335233、化合物

HRID 586714ノート

反応式

HRID 586714 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 22335233HCID 22335233、化合物

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒3 回

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2cab6c20059447128af231a092f394ae
出典データセット
uspto-grants-2005_08
特許番号
US06936619B2

反応ノート

読み込み中…