1,2-Dibromoethane → HCID 68650332, compound

HRID 1949108Notes

Reaction equation

HRID 1949108 reaction equation
[Br:1][CH2:2][CH2:3]Br.C([O-])([O-])=O.[Cs+].[Cs+].[C:11]([N:18]1[C:30]2[C:29]([OH:31])=[C:28]3[N:32]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C:33]4[CH:34]=[CH:35][C:36]([F:39])=[CH:37][C:38]=4[C:27]3=[CH:26][C:25]=2[C:24]2[C:19]1=[CH:20][CH:21]=[C:22]([F:47])[CH:23]=2)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>C(#N)C>[C:40]([N:32]1[C:28]2[C:29]([O:31][CH2:3][CH2:2][Br:1])=[C:30]3[N:18]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:19]4[CH:20]=[CH:21][C:22]([F:47])=[CH:23][C:24]=4[C:25]3=[CH:26][C:27]=2[C:38]2[C:33]1=[CH:34][CH:35]=[C:36]([F:39])[CH:37]=2)([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 67212243HCID 67212243, compound

Product 1

HCID 68650332HCID 68650332, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1,2-dibromoethane (>5 equiv) in acetonitrile was added Cs2CO3 (2 equiv) and 5,7-diBOC-2,10-difluoro-6-hydroxyindolo[2,3-b]carbazole (1 equiv) under argon. The suspension was refluxed and the reaction was monitored by TLC. After completion of the reaction (1-3 hours), the solid was removed by filteration and washed with dichloromethane. The combined filtrate was concentrated and the residue was subjected to chromatography on silica gel, eluting with 8% ethyl acetate in hexanes to give 5,7-diBOC-2,10-difluoro-6-(2-bromoethoxy)indolo[2,3-b]carbazole (77%). 1H NMR (400 MHz, CDCl3) δ ppm 8.13 (s, 1H), 8.06 (dd, J=9.0, 4.2 Hz, 2H), 7.68 (dd, J=8.4, 2.8 Hz, 2H), 7.17 (td, J=9.0, 2.8 Hz, 2H), 4.21 (t, J=6.8 Hz, 2H), 3.42 (t, J=7.0 Hz, 2H), 1.74 (s, 18H).

Workup

  1. temperatureThe suspension was refluxed
  2. customAfter completion of the reaction (1-3 hours)
  3. customthe solid was removed by filteration
  4. washwashed with dichloromethane
  5. concentrationThe combined filtrate was concentrated
  6. washeluting with 8% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-2881ecab11144e1bb6688c7aeee7d18e
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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