Dimethylformamide → HCID 12018130, compound

HRID 1017560Notes

Reaction equation

HRID 1017560 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=O)[O:13][C:14](=[O:31])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C@@H:24]3[CH2:28][O:27][C:26]([CH3:30])([CH3:29])[O:25]3)[CH:17]=2)=[CH:3]1.C[N:34](C=O)C>N.O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:13])[NH:34][C:14](=[O:31])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C@@H:24]3[CH2:28][O:27][C:26]([CH3:29])([CH3:30])[O:25]3)[CH:17]=2)=[CH:3]1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 12018132HCID 12018132, compound

Product 1

HCID 12018130HCID 12018130, compound

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

3-(1-Methylindol-3-yl)-4-[3-((R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyloxy)-phenyl]furan-2,5-dione (5.4 g, 13.7 mmol) was dissolved in DMF (50 mL) and was diluted with NH3 (aq.) (100 mL). The reaction mixture was then heated at 140° C. for 5 h, cooled to room temperature and then diluted with water. The product was extracted with EtOAc and the organic layer was washed with NaCl (sat.) and dried over sodium sulfate to give the crude product which was further purified by re-crystallization from dichloromethane and hexane to give 3-(1-methylindol-3-yl)-4-[3-((R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyloxy)phenyl]-1H-pyrrole-2,5-dione (5 g).

Workup

  1. temperaturecooled to room temperature
  2. extractionThe product was extracted with EtOAc
  3. washthe organic layer was washed with NaCl (sat.)
  4. dry with materialdried over sodium sulfate
  5. customto give the crude product which
  6. customwas further purified by re-crystallization from dichloromethane and hexane

Sources & evidence

ORD record
ord-9250cc2812a74c6e8ec064322c2ed857
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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