HCID 69315955, compound → HCID 178517439, compound

HRID 2117962Notes

Reaction equation

HRID 2117962 reaction equation
[Br:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([CH:8]2[C:12](=[O:13])[NH:11][C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:9]2[C:20](OCC)=[O:21])=[O:7])=[CH:4][CH:3]=1>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2[O:7][C:20](=[O:21])[C:9]3[C:8]=2[C:12](=[O:13])[NH:11][C:10]=3[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:25][CH:26]=1

Participants

3

Reactant 1

HCID 69315955HCID 69315955, compound

Product 1

HCID 178517439HCID 178517439, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
250 °C

Procedure

The p-bromobenzoylpyrrolinone ester 5 (154 mg, 0.37 mmol) was irradiated with microwave radiation (at a frequency of 2 to 45 GHz, and a forward power of 300 Watts) without solvent, heating to 250° C. for 10 minutes. The crude product was then allowed to cool, methanol was added and the solid filtered off and washed with methanol. This gave the furopyrrole 6 as a red solid (129 mg, 94%). M.p. 295° C. (subl., decomp.); δH (DMSO d6) 11.88 (1H, s, NH), 8.13-8.17 (2H, m, Ar—H), 7.98 and 7.66 (2×2H, AA′BB′, J 8.7, C6H4) and 7.43-7.47 (3H, m, Ar—H); m/z 370 (M+1 81Br, 94%) and 368 (M+1 79Br, 100%).

Workup

  1. temperatureto cool
  2. filtrationthe solid filtered off
  3. washwashed with methanol

Sources & evidence

ORD record
ord-1c057a7101fc44c79ce6f87f95e40097
Source dataset
uspto-grants-2008_10
Patent number
US07442804B2

Reaction notes

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