Boron tribromide → HCID 11561890, compound

HRID 2114500Notes

Reaction equation

HRID 2114500 reaction equation
[CH2:1]([N:3]([CH2:35][CH3:36])[C:4]([C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:22]3[CH2:27][CH2:26][N:25]([CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:24][CH2:23]3)[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[C:15]([O:20]C)[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:35]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:22]3[CH2:27][CH2:26][N:25]([CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:24][CH2:23]3)[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[C:15]([OH:20])[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:36]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 11641609HCID 11641609, compound

Product 1

HCID 11561890HCID 11561890, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 10-(1-benzyl-piperidin-4-yl)-6-methoxy-10H-phenoxazine-3-carboxylic acid diethylamide, 4d (50 mg, 0.1 mmol) in methylene chloride (2 mL) at 0° C. was added a 1M solution of boron tribromide in methylene chloride (0.8 mL, 0.8 mmol). The mixture was allowed to stir for 15 min at rt, followed by stirring at rt for 4 h. A saturated NaHCO3 solution and methylene chloride were added, and the organic phase was separated. The organic phase was dried, filtered, and evaporated. The residue was purified via reverse phase HPLC (eluent: CH3CN in water containing 0.1% TFA) to yield 17 mg (29%) of title compound 10-(1-benzyl-piperidin-4-yl)-6-hydroxy-10H-phenoxazine-3-carboxylic acid diethylamide, 6d as a TFA salt. MS m/z (MH+) 471.0.

Workup

  1. stirringby stirring at rt for 4 h
  2. customthe organic phase was separated
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified via reverse phase HPLC (eluent: CH3CN in water containing 0.1% TFA)

Sources & evidence

ORD record
ord-4238accf1bdd46a6b1c9cf1f7eeee5d7
Source dataset
uspto-grants-2008_10
Patent number
US07432257B2

Reaction notes

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