N-bromobutanimide → HCID 22050959, compound

HRID 1867096Notes

Reaction equation

HRID 1867096 reaction equation
[F:1][C:2]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[C:16]([O:18][CH3:19])=[O:17])[C:8](=[O:25])[CH:7]=1.[Br:31]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>>[Br:31][C:7]1[C:8](=[O:25])[N:9]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[C:16]([O:18][CH3:19])=[O:17])[C:10]([CH3:12])=[CH:11][C:6]=1[O:5][CH2:4][C:3]1[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:2]=1[F:1]

Participants

4

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 22050609HCID 22050609, compound

Product 1

HCID 22050959HCID 22050959, compoundYield 31%

Procedure

A 100 mL round bottomed flask equipped with stirbar and nitrogen inlet was charged with the product of Step 3 (2.1 g, 5.06 mmol) and N methyl 2-pyrrolidine (10 mL). N-Bromo succinimide (1 g, 5.56 mmol) was added and the reaction mixture was stirred at room temperature for 1 h. The mixture poured into saturated aqueous NaHCO3 and extracted with ethyl acetate. The organic layer was washed with brine, dried with Na2SO4, and concentrated in vacuo. The residue was chromatographed on silica (1:1 hexanes; ethyl acetate) to give the title compound as an orange oil (0.77 g, 31%). 1H NMR (400 MHz, CD3OD) δ 8.16 (app qd, J=2.5 and 7.2 Hz, 1H), 7.84 (d, J=2.6 Hz, 1H), 7.64 (m, 1H), 7.30 (d, J=9.2 Hz, 1H), 7.04 (appt, J=8.4 Hz, 2H), 6.60 (s, 1H), 5.33 (s, 2H), 3.80 (s, 6H), 1.99 (s, 3H) ppm. 19F NMR (400 MHz, CD3OD) δ −111.56 (1F), −116.00 (1F) ppm. ES-HRMS m/z 494.0398 (M+H calcd for C22H13BrF2NO5 requires 494.0409).

Workup

  1. customA 100 mL round bottomed flask equipped with stirbar and nitrogen inlet
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica (1:1 hexanes; ethyl acetate)

Sources & evidence

ORD record
ord-89af97576b054f2cb28520f90828253b
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

Loading…