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 73653Notes

Reaction equation

HRID 73653 reaction equation
[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]

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a7424c7c8c5d48d59a63217479856e0a
Source dataset
uspto-grants-2014_09
Patent number
US08829185B2

Reaction notes

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