Carbon tetrabromide → HCID 136383562, compound

HRID 2298248Notes

Reaction equation

HRID 2298248 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:21][CH2:22][CH2:23][N:24]1[C:32]2[C:27](=[CH:28][C:29]([F:33])=[CH:30][CH:31]=2)[C:26]([N:34]2[C:38]([C:39]3[C:47]4[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=4)[NH:41][CH:40]=3)=[N:37][NH:36][C:35]2=[O:48])=[CH:25]1.[Br:49]C(Br)(Br)Br>C1COCC1>[Br:49][CH2:21][CH2:22][CH2:23][N:24]1[C:32]2[C:27](=[CH:28][C:29]([F:33])=[CH:30][CH:31]=2)[C:26]([N:34]2[C:38]([C:39]3[C:47]4[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=4)[NH:41][CH:40]=3)=[N:37][NH:36][C:35]2=[O:48])=[CH:25]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromide2×HCID 11776Triphenylphosphine3×HCID 136383563HCID 136383563, compound

Product 1

HCID 136383562HCID 136383562, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (0.168, 0.64 mmol) was added to a mixture of 4-[1-(3-hydroxy-propyl)-5-fluoro-indol-3-yl]-5-(1-H-indol-3-yl)-2,4-dihydro-[1,2,4]triazol-3-one (0.23 g 0.59 mmol), synthesised in accordance to the procedure for Example 1, triphenylphosphine (0.168 g, 0.64 mmol) and tetrabromomethane (0.218 g, 0.66 mmol) in dry THF (15 ml). The resulting mixture was stirred at ambient temperature. After 16 h the LCMS showed that some starting material still was left. Additional tetrabromomethane (0.198 g, 0,60 mmol) and triphenylphosphine (0.158 g, 0.60 mmol) were added and the solution was allowed to proceed for 20 h more at ambient temperature. Evaporation and silica gel chromatography (dichloromethane/methanol, gradient to 100/5) afforded 0.165 g (57%) of the title compound as a white solid.

Workup

  1. waitstill was left
  2. waitto proceed for 20 h more at ambient temperature
  3. customEvaporation and silica gel chromatography (dichloromethane/methanol, gradient to 100/5)

Sources & evidence

ORD record
ord-473cd757d08e44259187a06cfbfd2fb1
Source dataset
uspto-grants-2002_12
Patent number
US06492406B1

Reaction notes

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