HCID 68183820, compound → HCID 68184017, compound

HRID 2199999Notes

Reaction equation

HRID 2199999 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:17]C)=[C:11]([C:14]([OH:16])=[O:15])[CH:12]=2)[C:7]([CH3:19])=[N:6]1.[Br-].[Br-].[Br-].B>C(Cl)Cl>[Cl:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:2]([Cl:1])[C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([OH:17])=[C:11]([C:14]([OH:16])=[O:15])[CH:12]=2)[C:7]([CH3:19])=[N:6]1

Participants

4

Reactant 2

HCID 68183820HCID 68183820, compoundHCID 178419136HCID 178419136, compound

Product 1

HCID 68184017HCID 68184017, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of the compound [179] (7.4 mg) in methylenechloride (0.2 mL) was added 1M methylenechloride solution of borane tribromide (0.2 mL) under ice-cooling, and then the reaction mixture was stirred at 0° C. for 3 hours. The reaction mixture was quenched with water, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by reverse phase preparative liquid chromatography to give the titled compound (3.7 mg) as a pale brown solid.

Workup

  1. temperaturecooling
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by reverse phase preparative liquid chromatography

Sources & evidence

ORD record
ord-9bba34ef01884e658ff92e770e5d68ca
Source dataset
uspto-grants-2016_06
Patent number
US09359350B2

Reaction notes

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