HCID 12085085, compound → HCID 12085086, compound

HRID 1358121Notes

Reaction equation

HRID 1358121 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]3[C:14]([O:15][CH:16]([F:18])[F:17])=[CH:13][CH:12]=[CH:11][C:7]=3[O:8][C:9](=[O:10])[C:4]=2[CH:3]=1.[Br-:21].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C1COCC1>[NH2:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]3[C:14]([O:15][CH:16]([F:18])[F:17])=[CH:13][CH:12]=[CH:11][C:7]=3[O:8][C:9](=[O:10])[C:4]=2[C:3]=1[Br:21]

Participants

4

Reactant 2

HCID 12085085HCID 12085085, compoundHCID 21124087Pyridiniumtribromide

Product 1

HCID 12085086HCID 12085086, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 27B (4.03 g, 14.54 mmol) in THF (200 mL) at room temperature was treated over 15 minutes with pyridinium tribromide (5.16 g, 15.26 mmol), stirred for 14 hours, and concentrated. The concentrate was treated with water (200 mL), stirred at room temperature for 15 minutes, and filtered. The resulting solid was washed with water (200 mL), suspended in hot CH3CN, cooled to room temperature, and filtered to provide a first crop of desired product. The filtrate was treated with charcoal, filtered, and concentrated to provide a solid which was suspended in diethyl ether and filtered to provide a second crop of desired product. MS (ESI(−)Q1MS) m/z 355 (M−H)−.

Workup

  1. concentrationconcentrated
  2. additionThe concentrate was treated with water (200 mL)
  3. stirringstirred at room temperature for 15 minutes
  4. filtrationfiltered
  5. washThe resulting solid was washed with water (200 mL)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-2b47fb67704f4831801193f3286cd38b
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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