Ammonium formate → methyl 4H-thieno(3,2-b)pyrrole-2-carboxylate

HRID 1363321노트

반응식

HRID 1363321 반응식
CN(C)[CH:3]=[CH:4][C:5]1[S:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][C:6]=1[N+:14]([O-])=O.C([O-])=O.[NH4+]>CO.[Pd]>[S:9]1[C:5]2[CH:4]=[CH:3][NH:14][C:6]=2[CH:7]=[C:8]1[C:10]([O:12][CH3:13])=[O:11]

참가 물질

5

반응물 2

HCID 2723923Ammonium formate3회HCID 72053195Methyl 5-(2-dimethylaminovinyl)-4-nitrothiophene-2-carboxylate

생성물 1

HCID 12110979methyl 4H-thieno(3,2-b)pyrrole-2-carboxylate수율 16%

시약·촉매·용매 2

HCID 23938Palladium촉매3회HCID 887Methanol용매

실험 절차

To a solution of methyl 5-(2-dimethylaminovinyl)-4-nitro-thiophene-2-carboxylate (0.698 g, 2.73 mmol) in MeOH (15.0 mL) were added ammonium formate (0.332 g, 5.26 mmol) and Pd/C (33.2 mg, 10% by weight). The mixture was refluxed for 6 h. Additional ammonium formate (0.664 g, 10.53 mmol) was added to the reaction and the mixture was refluxed for 20 h. Additional ammonium formate (0.664 g, 10.53 mmol) and Pd/C (0.1 g, 30% by weight) were added and the reaction mixture was refluxed for another 8 h. Additional Pd/C (0.1 g, 30% by weight) was added and the mixture was refluxed for another 16 h. The reaction was cooled and filtered through a Celite® plug. The filtrate was concentrated in vacuo, taken up in EtOAc (0.2 L) and washed with water, saturated aq NaCl, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by HPLC to obtain methyl 4H-thieno[3,2-b]pyrrole-2-carboxylate as a yellow solid (0.078 g, 16%). 1H NMR (400 MHz, CDCl3) δ (ppm) 8.40 (s, 1H) 7.71 (s, 1H) 7.20 (t, J=2.7 Hz, 1H) 6.50 (m, 1H), 3.90 (s, 3H).

후처리

  1. temperatureThe mixture was refluxed for 6 h
  2. temperaturethe mixture was refluxed for 20 h
  3. temperaturethe reaction mixture was refluxed for another 8 h
  4. temperaturethe mixture was refluxed for another 16 h
  5. temperatureThe reaction was cooled
  6. filtrationfiltered through a Celite® plug
  7. concentrationThe filtrate was concentrated in vacuo
  8. washwashed with water, saturated aq NaCl
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe crude product was purified by HPLC

출처 및 근거

ORD 기록
ord-69233f5d2a0c42959e91f927551ca542
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07884124B2

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