Dimethylformamide → Methyl 5-(3-aminophenyl)thiophene-2-carboxylate

HRID 650667노트

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HRID 650667 반응식
[S:1](O)(O)(=O)=O.[NH2:6][C:7]1[CH:8]=[C:9](B(O)O)[CH:10]=[CH:11][CH:12]=1.N[C:17]1[CH:18]=[C:19](B(O)O)C=C[CH:22]=1.[C:26](=[O:29])([O-])[O-].[Na+].[Na+].CN([CH:35]=[O:36])C>C(OCC)(=O)C>[CH3:26][O:29][C:35]([C:22]1[S:1][C:19]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([NH2:6])[CH:8]=2)=[CH:18][CH:17]=1)=[O:36]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 162111393-Aminophenylboronic Acid Hemisulfate

생성물 1

HCID 15541315Methyl 5-(3-aminophenyl)thiophene-2-carboxylate수율 48%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

A mixture of compound N-1 (1.6 g, 7.20 mmol), 3-aminophenylboronic acid hemisulfate (1.60 g, 8.60 mmol), Palladium tetrakis triphenylphosphine (0.25 g, 0.216 mmol), sodium carbonate (40 mL, 2M, 82 mmol) in DMF (100 mL) was stirred for 2 hrs at 80° C. overnight. The solvent was removed and the crude reaction product was taken up in ethyl acetate (40 mL). The solution was washed with 5% solution of hydrochloric acid (30 mL), then with saturated sodium chloride solution (30 mL), dried over sodium sulfate and evaporated. Purification of the residue on silica gel (1:1 hexanes-EtOAc) gave 0.790 g of compound N-2 (48% yield).

후처리

  1. customThe solvent was removed
  2. customthe crude reaction product
  3. washThe solution was washed with 5% solution of hydrochloric acid (30 mL)
  4. dry with materialwith saturated sodium chloride solution (30 mL), dried over sodium sulfate
  5. customevaporated
  6. customPurification of the residue on silica gel (1:1 hexanes-EtOAc)

출처 및 근거

ORD 기록
ord-ebde23dbf32c436b939272b7cfa9fdf2
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06274620B1

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