N-bromobutanimide → HCID 22050160, compound

HRID 1867093Notes

Reaction equation

HRID 1867093 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][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[F:23])[C:16]([O:18][CH3:19])=[O:17])[C:8](=[O:24])[CH:7]=1.[Br:30]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>>[Br:30][C:7]1[C:8](=[O:24])[N:9]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=2[F:23])[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:25]=[CH:26][C:27]([F:29])=[CH:28][C:2]=1[F:1]

Participants

4

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 22050189HCID 22050189, compound

Product 1

HCID 22050160HCID 22050160, compoundYield 40.2%

Procedure

A 100 mL round bottomed flask equipped with stirbar and nitrogen inlet was charged with methyl 3-[4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-fluorobenzoate (7.3 g, 18 mmol) and N-methyl-2-pyrrolidine (20 mL). N-Bromo succinimide (3.5 g, 19.8 mmol) was added and the reaction mixture was stirred at room temperature for 30 minutes. 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 triturated with diethyl ether and filtered to give the title compound as a white powder (3.49 g). 1H NMR (400 MHz, CD3OD) δ 8.16 (qd, J=3, 6.8 and 15.6 Hz, 1H), 7.84 (d, J=2.12 Hz, 1H), 7.64 (q, J=8.4 and 14.8 Hz, 1H), 7.29 (d, J=8.4 Hz, 1H), 7.04 (m, 2H), 6.60 (s, 1H), 5.34 (s, 2H), 3.87 (s, 3H), 2.00 (s, 3H) ppm. 19F NMR (400 MHz, CD3OD) δ −111.51 (1F), −115.98 (1F), −117.43 (1F) ppm. ES-HRMS m/z 494.0387 (M+H calcd for C22H19BrF2NOs 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 triturated with diethyl ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-934fe8113103453eb9b42ce6932ecd02
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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