N-bromobutanimide → HCID 10113225, compound

HRID 2416675Notes

Reaction equation

HRID 2416675 reaction equation
[C:1]([C:3]1[CH:25]=[CH:24][C:6]2[NH:7][C:8]3[N:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]([C:20]([F:23])([F:22])[F:21])([CH2:15][O:16][CH:17]([CH3:19])[CH3:18])[C:5]=2[CH:4]=1)#[N:2].C1C(=O)N([Br:33])C(=O)C1.CCOC(C)=O.CCCCCC>C(#N)C>[Br:33][C:11]1[CH:10]=[N:9][C:8]2[NH:7][C:6]3[CH:24]=[CH:25][C:3]([C:1]#[N:2])=[CH:4][C:5]=3[C:14]([C:20]([F:21])([F:22])[F:23])([CH2:15][O:16][CH:17]([CH3:19])[CH3:18])[C:13]=2[CH:12]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 21226206Ethyl acetate hexaneHCID 22633355HCID 22633355, compound

Product 1

HCID 10113225HCID 10113225, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 7-cyano-5-trifluoromethyl-5-isopropoxymethyl-5,10-dihydrobenzo[b][1,8]naphthyridine (14)(61 mg, 0.176 mmol) in anhydrous acetonitrile (2 mL) at room temperature was added NBS (38 mg, 0.211 mmol). The reaction mixture was stirred at room temperature for 1 h 30 min. The reaction was quenched with 1:1 saturated aqueous NaHCO3/water (20 mL), and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Flash chromatography (20%-30% EtOAc-Hexane) furnished 15 (73 mg, 97% yield) as an off-white solid: m.p. 76-77° C.; low resolution mass spectrum (ESI) m/z 426.2 [(M+H)+ calcd for C18H16BrF3N3O: 426.05].

Workup

  1. customThe reaction was quenched with 1:1 saturated aqueous NaHCO3/water (20 mL)
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3fa6f39856c2404eb66785dd5cd381fc
Source dataset
uspto-grants-2004_11
Patent number
US06825210B2

Reaction notes

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