Carbon tetrabromide → HCID 86760258, compound

HRID 2215798Notes

Reaction equation

HRID 2215798 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[C:6]2[C:10](=[C:11]3[C:23]4=[CH:24][N:25]([CH3:28])[C:26](=[O:27])[C:22]4=[C:21]4[C:13]([NH:14][C:15]5[CH:16]=[CH:17][C:18](=[O:29])[CH2:19][C:20]=54)=[C:12]3[CH:30]=1)[N:9]=[CH:8][CH:7]=2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:51]>CN(C=O)C.CCOC(C)=O>[Br:51][CH2:2][CH2:3][CH2:4][C:5]1[C:6]2[C:10](=[C:11]3[C:23]4=[CH:24][N:25]([CH3:28])[C:26](=[O:27])[C:22]4=[C:21]4[C:13]([NH:14][C:15]5[CH:16]=[CH:17][C:18](=[O:29])[CH2:19][C:20]=54)=[C:12]3[CH:30]=1)[N:9]=[CH:8][CH:7]=2

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86760259HCID 86760259, compound

Product 1

HCID 86760258HCID 86760258, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 13-(3-hydroxypropyl)-5-methyl-7H-indolo[6,7-a]pyrrolo[3,4-c]-carbazole-6,8-dione (1.18 g, 2.97 mmol) in DMF (45 mL) was added triphenylphosphine (1.17 g, 4.45 mmol) followed by carbon tetrabromide (1.48 g, 4.45 mmol). The resulting solution was allowed to stir at room temperature for 30 min. The solution was diluted with EtOAc (200 mL) and washed with water (2×200 mL) and brine (200 mL). The combined aqueous layers were washed with EtOAc (100 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated to a red-orange solid. Flash chromatography (SiO2, 20% EtOAc/hexanes) gave the title compound (1.05 g, 77%) as an orange solid, mp 238 C. 1H NMR (DMSO-d6)11.15 (s, 1H), 9.16 (d, J=7.5 Hz, 1H), 8.36 (d, J=9 Hz, 1H), 8.04 (d, J=9 Hz, 1H), 7.93 (d, J=7.5 Hz, 1H), 7.60–7.67 (m, 2H), 7.44 (dd, J=7.5, 7.5 Hz, 1H), 6.85 (d, J=3 Hz, 2H), 5.03 (t, J=7 Hz, 2H), 3.85 (s, 3H), 3.72 (t, J=7 Hz, 2H), 2.50 (m, 2H, partially buried under DMSO signal). MS (atmospheric pressure chemical ionization, m/z) 460, 462 [C24H18BrN3O2+H]+.

Workup

  1. washwashed with water (2×200 mL) and brine (200 mL)
  2. washThe combined aqueous layers were washed with EtOAc (100 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to a red-orange solid

Sources & evidence

ORD record
ord-58aa2b5248c541d5bf05772bc8a99a44
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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