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Triphenylphosphine → 3-[(4-Methoxyphenyl)amino]-1-[(5-methylisoxazol-3-yl)methyl]-4-phenyl-1H-pyrrole-2,5-dione

HRID 2113770
Notes
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Reaction equation

HRID 2113770 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:11](=[O:22])[NH:12][C:13](=[O:21])[C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.[CH3:23][C:24]1[O:28][N:27]=[C:26]([CH2:29]O)[CH:25]=1.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]2[C:11](=[O:22])[N:12]([CH2:29][C:26]3[CH:25]=[C:24]([CH3:23])[O:28][N:27]=3)[C:13](=[O:21])[C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2736567(5-Methyl-1,2-oxazol-3-yl)methanolHCID 691437143-[(4-methoxyphenyl)amino]-4-phenyl-1H-pyrrole-2,5-dione

Product 1

HCID 113726913-[(4-Methoxyphenyl)amino]-1-[(5-methylisoxazol-3-yl)methyl]-4-phenyl-1H-pyrrole-2,5-dioneYield 21.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
130 °C

Procedure

To a solution of 3-[(4-methoxyphenyl)amino]-4-phenyl-1H-pyrrole-2,5-dione (0.17 mmol, 50 mg), 5-methylisoxazole-3-methanol (0.19 mmol, 21 mg) and diethyl azodicarboxylate (0.19 mmol, 33 mg) in dry THF (1 mL) was added triphenylphosphine (0.19 mmol, 49 mg) in dry THF (1 mL). The mixture was heated in a microwave reactor at 130° C. for six min. After cooling, the reaction mixture was purified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN) to give 14 mg (21%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 7.23 (bs, 1H), 7.16-7.06 (m, 3H), 7.01-6.96 (m, 2H), 6.63-6.53 (m, 4H), 6.03 (d, J=0.7 Hz, 1H), 4.82 (s, 2H), 3.70 (s, 3H), 2.39 (d, J=0.7 Hz, 3H).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was purified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN)

Sources & evidence

ORD record
ord-1ee0ba7a571e4eba96b96934a218d55b
Source dataset
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07432288B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes