ethyl 5-carbamoyl-4-(3-fluoro-4-nitrophenyl)-1H-pyrrole-3-carboxylate → ethyl 5-cyano-4-(3-fluoro-4-nitrophenyl)-1H-pyrrole-3-carboxylate

HRID 1094846노트

반응식

HRID 1094846 반응식
[NH2:1][C:2]([C:4]1[NH:8][CH:7]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:5]=1[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[C:16]([F:23])[CH:15]=1)=O>O=P(Cl)(Cl)Cl>[C:2]([C:4]1[NH:8][CH:7]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:5]=1[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[C:16]([F:23])[CH:15]=1)#[N:1]

참가 물질

3

반응물 1

HCID 57955150ethyl 5-carbamoyl-4-(3-fluoro-4-nitrophenyl)-1H-pyrrole-3-carboxylate

생성물 1

HCID 57758340ethyl 5-cyano-4-(3-fluoro-4-nitrophenyl)-1H-pyrrole-3-carboxylate수율 97.5%

시약·촉매·용매 1

HCID 24813Phosphorus oxychloride용매

실험 절차

A solution of intermediate ethyl 5-(aminocarbonyl)-4-(3-fluoro-4-nitrophenyl)-1H-pyrrole-3-carboxylate (36.8 mg, 114.5 mmol) in POCl3 (500 mL) was heated to 70° C. for 2 h. TLC analysis indicated that there was complete conversion of starting material. Excess POCl3 was removed under reduced pressure and the remaining solids were poured over ice. The pH was adjusted to 8 using 5 N NaOH and the solution was filtered. The product was dried over night under reduced pressure to afford a light brown solid (33.85 g, 111.6 mmol) in 97% yield. 1H-NMR (DMSO-d6) δ 13.32 (br s, 1H), 8.21 (app t, J=8.4 Hz, 1H), 7.90 (s, 1H), 7.73 (dd, J=12.4, 2.0 Hz, 1H), 7.51 (m, 1H), 4.13 (q, J=7.2 Hz, 2H), 1.15 (t, J=7.2 Hz, 3H); HPLC RT=3.16 min.

후처리

  1. customExcess POCl3 was removed under reduced pressure
  2. additionthe remaining solids were poured over ice
  3. filtrationthe solution was filtered
  4. customThe product was dried over night under reduced pressure

출처 및 근거

ORD 기록
ord-ea7e74f7d2b743beaa5bb143bccbadb3
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133995B2

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