Bromide ion → HCID 86624802, compound

HRID 494152Notes

Reaction equation

HRID 494152 reaction equation
[C:1]([C:4]1[C:9]2[N:10]3[CH2:24][CH2:23][N:22]([CH3:25])[C:21](=[O:26])[C:11]3=[C:12]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]=2[C:7](=[O:27])[N:6]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[C:31]([Cl:36])[CH:30]=2)[N:5]=1)(=[O:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Br:47]Br.[Br-]>C1COCC1>[Br:47][CH2:2][C:1]([C:4]1[C:9]2[N:10]3[CH2:24][CH2:23][N:22]([CH3:25])[C:21](=[O:26])[C:11]3=[C:12]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]=2[C:7](=[O:27])[N:6]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[C:31]([Cl:36])[CH:30]=2)[N:5]=1)=[O:3]

Participants

6

Reactant 4

HCID 259Bromide ionHCID 24408Bromine2×HCID 2733832Lithium Hexamethyldisilazide2×HCID 68865364HCID 68865364, compound

Product 1

HCID 86624802HCID 86624802, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a cold (0° C.) solution of 4-acetyl-10-(benzyloxy)-2-(3-chloro-4-fluorobenzyl)-8-methyl-7,8-dihydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (0.50 g, 0.98 mmol) in anhydrous THF (20 mL) under an atmosphere of nitrogen, a solution of lithium bis(trimethylsilyl)amide (1.08 mL, 1.08 mmol) in THF was added. After stirring at the same temperature for 15 minutes, bromine (0.24 g, 1.47 mmol) was added and the reaction was stirred at room temperature. The reaction was monitored by LC-MS. Additional solution of lithium bis(trimethylsilyl)amide and bromine were added to drive the reaction to completion. The bromide generated as a solution in THF was used in the following reaction without further workup or purification. ES MS M+1=587

Workup

  1. stirringthe reaction was stirred at room temperature
  2. customthe reaction to completion
  3. customwas used in the following reaction without further workup or purification

Sources & evidence

ORD record
ord-a47cc77a3fb842a7a068d2d69abb0c5e
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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