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

HRID 650667ノート

反応式

HRID 650667 の反応式
[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]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 162111393-Aminophenylboronic Acid Hemisulfate

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ebde23dbf32c436b939272b7cfa9fdf2
出典データセット
uspto-grants-2001_08
特許番号
US06274620B1

反応ノート

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