Bromine → HCID 90408910, compound

HRID 516567Notes

Reaction equation

HRID 516567 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Si](C)(C)C)=[C:13]([F:21])[CH:12]=2)[N:8]=[C:7]([C:22]([O:24][CH3:25])=[O:23])[C:6]=1[Cl:26])(=[O:3])[CH3:2].[Br:27]Br.[O-]S([O-])=O.[Na+].[Na+]>ClCCl>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Br:27])=[C:13]([F:21])[CH:12]=2)[N:8]=[C:7]([C:22]([O:24][CH3:25])=[O:23])[C:6]=1[Cl:26])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24408BromineHCID 24437Sodium SulfiteHCID 90408191HCID 90408191, compound

Product 1

HCID 90408910HCID 90408910, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 100-mL round bottom flask, equipped with a stir bar was added methyl 4-acetamido-3-chloro-6-(3-fluoro-4-(trimethylsilyl)phenyl)picolinate (433 mg, 1.11 mmol), dichloromethane (10 mL) and bromine (0.225 mL, 4.39 mmol). The reaction was allowed to stir at room temperature for 18 hrs. The reaction was then poured into 1 N Na2SO3 and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated. The resulting residue was purified by flash chromatography (0-50% EtOAc in Hexanes) to afford the title compound as a light tan solid (0.440 g, 100%): 1H NMR (400 MHz, DMSO-d6) δ 10.02 (s, 1H), 8.71 (s, 1H), 7.98-7.81 (m, 2H), 7.74 (dd, J=8.4, 2.1 Hz, 1H), 3.94 (s, 3H), 2.23 (s, 3H); 19F NMR (376 MHz, DMSO-d6) δ −107.44; ESIMS m/z 402 [(M+H)+].

Workup

  1. customTo a 100-mL round bottom flask, equipped with a stir bar
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash chromatography (0-50% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-da147cac36914990a3181f772c7d0971
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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