Carbon tetrabromide → HCID 21949955, compound

HRID 2215812Notes

Reaction equation

HRID 2215812 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][CH:11]=[C:10]2[C:14]1[C:15](=[O:30])[NH:16][C:17](=[O:29])[C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:27]=1[N:26]([CH3:28])[CH:25]=[CH:24]2.O1CCCC1.C(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:59]>C(Cl)Cl>[Br:59][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][CH:11]=[C:10]2[C:14]1[C:15](=[O:30])[NH:16][C:17](=[O:29])[C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:27]=1[N:26]([CH3:28])[CH:25]=[CH:24]2

Participants

6

Reactant 4

HCID 11205Carbon tetrabromide3×HCID 11776Triphenylphosphine3×HCID 21919333Tetrahydrofurane dichloromethaneHCID 21949957HCID 21949957, compound

Product 1

HCID 21949955HCID 21949955, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[7-(3-hydroxypropyl)-1H-indol-3-yl]-4-(1-methyl-1H-indol-7-yl)pyrrole-2,5-dione (505 mg, 1.27 mmol) in 1:1 tetrahydrofuran/methylene chloride (60 mL) was added triphenylphosphine (330 mg, 1.25 mmol) followed by carbon tetrabromide (418 mg, 1.26 mmol). After one hour, additional triphenylphosphine (332 mg, 1.27 mmol) and carbon tetrabromide (414 mg, 1.25 mmol) was added. After 1 h, triphenylphosphine (330 mg, 1.26 mmol) and carbon tetrabromide (430 mg, 1.30 mmol) was added and stirred for 1 h. The reaction mixture was diluted with methylene chloride (100 mL), washed with saturated aq NaHCO3 (100 mL), brine (100 mL), dried (MgSO4) and concentrated. Flash chromatography (SiO2, 30% EtOAc/hexanes) gave the title compound (462 mg, 91%) as a red solid. 1H NMR (CDCl3) 8.93 (m, 1H), 8.66 (m, 1H), 8.07–7.87 (m, 4H), 6.64 (m, 1H), 6.49 (m, 2H), 3.72 (s, 3H), 3.41 (m, 2H), 2.96 (m, 2H), 2.21 (m, 2H). MS (electrospray, m/z) 464/462 (C24H20BrN3O2+H)+.

Workup

  1. waitAfter 1 h
  2. washwashed with saturated aq NaHCO3 (100 mL), brine (100 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ad6fa7a091844ba09cb3cbf8b4569fd4
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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