N-bromobutanimide → HCID 22050577, compound

HRID 1867104Notes

Reaction equation

HRID 1867104 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:11]=1[CH2:12][O:13][C:14]1[CH:19]=[C:18]([CH3:20])[N:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:29])[F:28])[C:16](=[O:31])[CH:15]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][C:15]1[C:16](=[O:31])[N:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:29])([F:28])[F:30])[C:18]([CH3:20])=[CH:19][C:14]=1[O:13][CH2:12][C:11]1[CH:32]=[CH:33][C:34]([F:36])=[CH:35][C:10]=1[F:9]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 22050960HCID 22050960, compound

Product 1

HCID 22050577HCID 22050577, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-bromosuccinimide (0.24 g, 1.36 mmol) was added into 4-[(2,4-difluorobenzyl)oxy]-6-methyl-1-[2-(trifluoromethyl)phenyl]pyridin-2(1H)-one (0.54 g, 1.36 mmol) in 20 ml of dichloromethane. The mixture was stirred at room temperature for 2 hours. Saturated sodium bicarbonate solution (150 ml) was added into the reaction mixture and the combine solution was transferred to a separatory funnel. The product was extracted with ethyl acetate (250 ml). The ethyl acetate solution was dried over anhydrous magnesium sulfate and evaporated to dryness. 1H NMR (400 MHz, CDCl3) δ 7.82 (d, J=7.25 Hz, 1H), 7.7 (app t, J=7.66 Hz, 1H), 7.60 (m, 2H), 7.26 (s, 1H), 6.97 (m, 1H), 6.87 (m, 1H), 6.09 (s, 1H), 5.25 (app d, J=3.35 Hz, 2H), 1.94 (s, 3H); LC/MS, tr=2.84 minutes (5 to 95% acetonitrile/water over 5 minutes at 1 ml/min with detection 254 nm, at 50° C.). ES-HRMS m/z 474.0113 (M+H calcd for C20H14BrF5NO2 requires 474.0123).

Workup

  1. customthe combine solution was transferred to a separatory funnel
  2. extractionThe product was extracted with ethyl acetate (250 ml)
  3. dry with materialThe ethyl acetate solution was dried over anhydrous magnesium sulfate
  4. customevaporated to dryness
  5. customLC/MS, tr=2.84 minutes (5 to 95% acetonitrile/water over 5 minutes at 1 ml/min with detection 254 nm, at 50° C.)

Sources & evidence

ORD record
ord-9a5fd62d4382479da8a9376b682dabef
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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