Pyridine → 5-Bromo-3,4-difluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid pentafluorophenyl ester

HRID 2218437ノート

反応式

HRID 2218437 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 233984895-Bromo-3,4-difluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid pentafluorophenyl ester収率 90.5%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e1152c4879d140fd8565efa6d85df8bb
出典データセット
uspto-grants-2008_08
特許番号
US07411001B2

反応ノート

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