Dimethylformamide → HCID 21950054, compound

HRID 2215804Notes

Reaction equation

HRID 2215804 reaction equation
O[CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[C:7]([C:16]2[C:17](=[O:32])[NH:18][C:19](=[O:31])[C:20]=2[C:21]2[CH:22]=[CH:23][CH:24]=[C:25]3[C:29]=2[N:28]([CH3:30])[CH:27]=[CH:26]3)=[CH:6]1.CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:58]>CCOC(C)=O.O>[Br:58][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[C:7]([C:16]2[C:17](=[O:32])[NH:18][C:19](=[O:31])[C:20]=2[C:21]2[CH:22]=[CH:23][CH:24]=[C:25]3[C:29]=2[N:28]([CH3:30])[CH:27]=[CH:26]3)=[CH:6]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21950067HCID 21950067, compound

Product 1

HCID 21950054HCID 21950054, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[1-(3-hydroxypropyl)-6-methoxy-1H-indol-3-yl]-4-(1-methyl-1H-indol-7-yl)-pyrrole-2,5-dione (3.0 g, 7.0 mmol) in solution of DMF (300 mL) was added PPh3 (2.6 g, 10.5 mmol) and CBr4 (3.3 g, 10.5 mmol). The reaction mixture was stirred at room temperature and under nitrogen for 1 h. The reaction was monitored by TLC and was completed after 2 h. The reaction mixture was diluted with EtOAc (300 mL) and water (800 mL). The aqueous phase was extracted with EtOAc (3×300 ml). The combined organic phases were washed with saturated aq NaHCO3 (300 mL), brine (500 mL) dried (MgSO4), filtered and concentrated. Flash chromatography (SiO2, 30% EtOAc/hexanes) gave the title compound (2.4 g, 71%) as a red solid. 1H NMR (300 MHz, DMSO-d6) 11.04 (s, 1H), 7.88 (s, 1H), 7.62 (d, J=6.1 Hz, 1H), 7.19 (d, J=2.6 Hz, 1H), 7.00–6.91 (m, 2H), 6.84 (d, J=6.0 Hz, 1H), 6.48 (d, J=2.5 Hz, 1H), 6.10 (m, 2H), 4.27 (t, J=5.8 Hz, 2H), 3.71 (s, 3H), 3.62 (s, 3H), 3.32 (t, J=5.8 Hz, 2H), 2.11 (m, 2H). MS (electrospray, m/z) 492.1/494.1 (M++1), 490.2/492.2 (M−−1).

Workup

  1. waitwas completed after 2 h
  2. extractionThe aqueous phase was extracted with EtOAc (3×300 ml)
  3. washThe combined organic phases were washed with saturated aq NaHCO3 (300 mL), brine (500 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bf4dcc74b72f433789e0a2f6896ddb4a
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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