Dimethylformamide → HCID 53946632, 화합물

HRID 1459633노트

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HRID 1459633 반응식
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

참가 물질

8

반응물 4

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

생성물 1

HCID 53946632HCID 53946632, 화합물

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 6212Chloroform용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ae9eb7c78185463e975496bacac934ba
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05854264

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