Pyridine → HCID 23398489, compound

HRID 2218437Notes

Reaction equation

HRID 2218437 reaction equation
[Br:1][C:2]1[C:3]([F:21])=[C:4]([F:20])[C:5]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([I:18])=[CH:14][C:13]=2[CH3:19])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].N1C=CC=CC=1.FC(F)(F)C(O[C:33]1[C:38]([F:39])=[C:37]([F:40])[C:36]([F:41])=[C:35]([F:42])[C:34]=1[F:43])=O>CN(C)C=O.CCOCC>[F:39][C:38]1[C:33]([O:8][C:7](=[O:9])[C:6]2[CH:10]=[C:2]([Br:1])[C:3]([F:21])=[C:4]([F:20])[C:5]=2[NH:11][C:12]2[CH:17]=[CH:16][C:15]([I:18])=[CH:14][C:13]=2[CH3:19])=[C:34]([F:43])[C:35]([F:42])=[C:36]([F:41])[C:37]=1[F:40]

Participants

6

Reactant 3

HCID 1049PyridineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 98907755-Bromo-3,4-difluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid

Product 1

HCID 23398489HCID 23398489, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-Bromo-3,4-difluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid (prepared as described in WO 99/01426) (1.61 g, 3.4 mmol) and pyridine (0.31 mL, 3.83 mmol) in anhydrous dimethylformamide (7 mL) was added pentafluorophenyl trifluoroacetate (0.71 mL, 4.13 mmol). The resultant solution was stirred at ambient temperature for 18 h. The reaction mixture was diluted with ether (100 mL) and washed with water (40 mL), 0.1 M aqueous hydrochloric acid (40 mL), saturated aqueous sodium bicarbonate (40 mL), and saturated brine (40 mL). The organics were dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a foam that was purified on silica gel. Elution with hexanes-ethyl acetate (19:1) afforded 5-Bromo-3,4-difluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid pentafluorophenyl ester (1.95 g, 89%) as a pale-yellow powder: 1H NMR (400 MHz, CDCl3) δ 8.59 (s, 1 H), 8.24 (d, J=5.8 Hz, 1 H), 7.54 (s, 1 H), 7.45 (d, J=8.4 Hz, 1 H), 6.70 (dd, J=8.4, 5.3 Hz, 1 H), 2.26 (s, 3 H).

Workup

  1. washwashed with water (40 mL), 0.1 M aqueous hydrochloric acid (40 mL), saturated aqueous sodium bicarbonate (40 mL), and saturated brine (40 mL)
  2. dry with materialThe organics were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto afford a foam that
  5. customwas purified on silica gel
  6. washElution with hexanes-ethyl acetate (19:1)

Sources & evidence

ORD record
ord-e1152c4879d140fd8565efa6d85df8bb
Source dataset
uspto-grants-2008_08
Patent number
US07411001B2

Reaction notes

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