HCID 12085085, compound → HCID 12085086, compound

HRID 2269793Notes

Reaction equation

HRID 2269793 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-e0527eab1048462a96da13e4c25329fd
Source dataset
uspto-grants-2001_12
Patent number
US06329534B1

Reaction notes

Loading…