N-bromobutanimide → 4-Bromo-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1-triisopropylsilyl-1H-pyrrole

HRID 1244989Notes

Reaction equation

HRID 1244989 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]([Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])[CH:18]=[CH:19][C:20]=2[C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[CH:12][CH:11]=1>O1CCCC1>[Br:1][C:19]1[C:20]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[C:16]([C:13]2[CH:12]=[CH:11][C:10]([F:9])=[CH:15][CH:14]=2)[N:17]([Si:27]([CH:31]([CH3:33])[CH3:32])([CH:34]([CH3:36])[CH3:35])[CH:28]([CH3:29])[CH3:30])[CH:18]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 219227124-{2-(4-Fluorophenyl)-1-[tri(propan-2-yl)silyl]-1H-pyrrol-3-yl}pyridine

Product 1

HCID 219227844-Bromo-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1-triisopropylsilyl-1H-pyrroleYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 8.61 g (47.4 mmol) of N-bromosuccinimide in 100 ml of tetrahydrofuran was added to a solution of 18.70 g (47.4 mmol) of 2-(4-fluorophenyl)-3-(pyridin-4-yl)-1-triisopropylsilyl-1H-pyrrole [prepared as described in step 7(ii) above] in 300 ml of tetrahydrofuran at −78° C., after which the resulting mixture was stirred at the same temperature for 6 hours. After removal of the cooling bath, the mixture was then stirred at room temperature for a further 1 hour. At the end of this time, 400 ml of hexane was added to the reaction mixture and the insoluble material was removed by filtration. The resulting filtrate was concentrated by evaporation under reduced pressure and the residue thus obtained was purified by chromatography on a silica gel column using a 2:1 by volume mixture of hexane and ethyl acetate as the eluant to give 9.57 g (yield 43%) of the title compound as pale yellow prismatic crystals.

Workup

  1. customAfter removal of the cooling bath
  2. stirringthe mixture was then stirred at room temperature for a further 1 hour
  3. additionAt the end of this time, 400 ml of hexane was added to the reaction mixture
  4. customthe insoluble material was removed by filtration
  5. concentrationThe resulting filtrate was concentrated by evaporation under reduced pressure
  6. customthe residue thus obtained
  7. customwas purified by chromatography on a silica gel column
  8. additionby volume mixture of hexane and ethyl acetate as the eluant

Sources & evidence

ORD record
ord-18a598c1e8834aefa55fcb302198cd39
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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