Carbon tetrabromide → 3-[1-(2-Bromoethyl)-6-methoxy-1H-indol-3-yl]-4-(1-methyl-1H-indol-7-yl)pyrrole-2,5-dione

HRID 2215802Notes

Reaction equation

HRID 2215802 reaction equation
O[CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[C:6]([C:15]2[C:16](=[O:31])[NH:17][C:18](=[O:30])[C:19]=2[C:20]2[CH:21]=[CH:22][CH:23]=[C:24]3[C:28]=2[N:27]([CH3:29])[CH:26]=[CH:25]3)=[CH:5]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:52]>C(Cl)Cl.C1COCC1.CCOC(C)=O>[Br:52][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[C:6]([C:15]2[C:16](=[O:31])[NH:17][C:18](=[O:30])[C:19]=2[C:20]2[CH:21]=[CH:22][CH:23]=[C:24]3[C:28]=2[N:27]([CH3:29])[CH:26]=[CH:25]3)=[CH:5]1

Participants

7

Reactant 3

HCID 11205Carbon tetrabromide2×HCID 11776Triphenylphosphine2×HCID 219499793-[1-(2-Hydroxyethyl)-6-methoxy-1H-indol-3-yl]-4-(1-methyl-1H-indol-7-yl)-pyrrole-2,5-dione

Product 1

HCID 219499533-[1-(2-Bromoethyl)-6-methoxy-1H-indol-3-yl]-4-(1-methyl-1H-indol-7-yl)pyrrole-2,5-dioneYield 77%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[1-(2-hydroxyethyl)-6-methoxy-1H-indol-3-yl]-4-(1-methyl-1H-indol-7-yl)pyrrole-2,5-dione (7.3 g, 17.7 mmol) in a mixture of CH2Cl2 (360 mL) and THF (240 mL) was added PPh3 (4.6 g, 17.7 mmol) and CBr4 (5.8 g, 17.7 mmol). The reaction mixture was stirred at room temperature and under nitrogen for 1 h. Another equivalent of PPh3 (4.6 g, 17.7 mmol) was added followed by an equivalent of CBr4 (5.8 g, 17.7 mmol). This operation was repeated one more time after 1 h. The reaction was monitored by TLC and was completed after 1 h. The reaction mixture was diluted with EtOAc (300 mL) and washed with saturated aqueous NaHCO3 (500 mL), and brine (500 mL). The organic solution was dried (MgSO4), filtered and concentrated. Flash chromatography (SiO2, 50% EtOAc/hexanes) gave the title compound (6.5 g, 77%) as a red solid. 1H NMR (300 MHz, DMSO-d6) 11.08 (s, 1H), 7.95 (s, 1H), 7.61 (d, J=7.8 Hz, 1H), 7.23 (d, J=3.1 Hz, 1H), 7.03–6.96 (m, 3H), 6.88 (d, J=6.2 Hz, 1H), 6.47 (d, J=3.1 Hz, 1H), 6.13 (s, 1H), 4.60 (t, J=6.0 Hz, 2H), 3.81 (t, J=6.0 Hz, 2H), 3.69 (s, 3H), 3.65 (s, 3H).

Workup

  1. customafter 1 h
  2. waitwas completed after 1 h
  3. washwashed with saturated aqueous NaHCO3 (500 mL), and brine (500 mL)
  4. dry with materialThe organic solution was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-08a21b5f634c4d33b162e1c359c4c554
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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