Dimethylformamide → HCID 53946632、化合物

HRID 1459633ノート

反応式

HRID 1459633 の反応式
CN(C=O)C.I[C:7]1[C:12]([CH3:13])=[N:11][CH:10]=[CH:9][N:8]=1.[CH:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)=[O:15].CCN(CC)CC>CC([O-])=O.CC([O-])=O.[Pd+2].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(Cl)(Cl)Cl>[CH3:13][C:12]1[C:7]([C:19]2[CH:20]=[CH:21][C:16]([CH:14]=[O:15])=[CH:17][CH:18]=2)=[N:8][CH:9]=[CH:10][N:11]=1

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 5910734-Formylphenylboronic AcidHCID 108786642-IODO-3-METHYLPYRAZINE

生成物 1

HCID 53946632HCID 53946632、化合物

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 6212Chloroform溶媒

反応条件

温度
90 °C

実験手順

To a 100 ml round bottomed flask with stirring bar and an argon inlet was added Pd(OAc)2 (0.036 g, 0.15 mmol), bisdiphenylphosphinoferrocene (DPPF, 0.12 g, 0.2 mmol), and 15 ml of DMF were heated to 50° for 15 minutes. Cooled the reaction to room temperature then added 2-iodo-3-methyl-pyrazine (1.2 g, 5.4 mmol)(5). (a prep from Albert Hirschberg et al. J.Org. Chem. Jun.,1961 p1907-1912) and 4-formylbenzenboronic acid (0.90 g, 6.0 mmol) and Et3N (1.05 ml, 7.5 mmol). The mixture was heated to 90° C. for 10 h. Removed solvent in vacuo, taken up with CHCl3 and washed with diluted NH4OH. The organic layer was dried (MgSO4), filtered and concentrated to yield a black oil. This material was chromatographed (silica gel, 30% EtOAc/Hexane) to afford the title product.

後処理

  1. temperaturewere heated to 50° for 15 minutes
  2. temperatureCooled
  3. customthe reaction to room temperature
  4. washwashed with diluted NH4OH
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a black oil
  9. customThis material was chromatographed (silica gel, 30% EtOAc/Hexane)

出典と根拠

ORDレコード
ord-ae9eb7c78185463e975496bacac934ba
出典データセット
uspto-grants-1998_12
特許番号
US05854264

反応ノート

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