N-bromobutanimide → HCID 54724161, compound

HRID 1831960Notes

Reaction equation

HRID 1831960 reaction equation
FC1C=C(F)C=CC=1C[O:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([O:18][CH3:19])=[O:17])[C:8](=[O:23])[CH:7]=1.BrN1C(=O)CCC1=O>C(#N)C>[OH:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([O:18][CH3:19])=[O:17])[C:8](=[O:23])[CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22049981HCID 22049981, compound

Product 1

HCID 54724161HCID 54724161, compoundYield 165.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 3-[4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]benzoate (from step 2) (15.85 g, 41.130 mmol) suspended in acetonitrile (165 mL) was cooled in an ice-bath. N-bromosuccinimide (7.687 g, 43.186 mmol) was added and the ice-bath was removed. The reaction mixture was stirred for 1.5 hours at room temperature. Reaction was concentrated and subjected to chromatography (silica gel, ethyl acetate with 10% methanol/hexanes) afforded an off white solid (17.63 g, 92%). 1H NMR (400 MHz, CDCl3) δ 8.17 (dt, J=1.41, 7.85 Hz, 1H), 7.90 (t, J=1.81 Hz, 1H), 7.67-7.41 (m, 3H), 7.05-6.88 (m, 2H), 6.13 (s, 1H), 5.30 (s, 2H), 3.95 (s, 1H), 2.01 (s, 3H). ES-HRMS m/z 464.0286 (M+H C21H16BrF2NO4 requires 464.0304).

Workup

  1. temperaturewas cooled in an ice-bath
  2. customthe ice-bath was removed
  3. customReaction
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-8c6f93ccdd624be2a0cb9c3d42181fbc
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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