Dichloroacetic Acid → (3-fluorobenzyl)-3-iodo-1H-pyridin-2-one

HRID 1831945ノート

反応式

HRID 1831945 の反応式
FC1C=C(F)C=CC=1CO[C:6]1[CH:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[C:8](=[O:20])[CH:7]=1.[I:26]N1C(=O)CCC1=O.ClC(Cl)C(O)=O>CC#N>[F:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][N:9]1[CH:10]=[CH:11][CH:6]=[C:7]([I:26])[C:8]1=[O:20]

参加物

5

反応物 3

HCID 6597Dichloroacetic AcidHCID 120273N-IodosuccinimideHCID 22050302HCID 22050302、化合物

生成物 1

HCID 79784710(3-fluorobenzyl)-3-iodo-1H-pyridin-2-one収率 106%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

To a mixture of 4-(2,4-difluorobenzyloxy)-1-(3-fluorobenzyl)-1H-pyridin-2-one (0.15 g, 0.43 mmol) and N-iodosuccinimide (0.10 g, 0.46 mmol) in CH3CN (3 mL) was added dichloroacetic acid (13 mg, 0.10 mmol), and the reaction mixture was heated to 60° C. for 4 h. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and the residue was dissolved in methylene chloride. The organic solution was washed with a saturated solution of NaHCO3 and then brine, dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography (silica, eluent 90:10 methylene chloride/hexanes to 99:1 methylene chloride/methanol) provided 4-(2,4-difluorobenzyloxy)-[(3-fluorobenzyl)-3-iodo-1H-pyridin-2-one as a white solid (0.15 g, 77%): mp 164-167° C.; 1H NMR (300 MHz, CDCl3) δ 7.65-7.55 (m, 1H), 7.35-7.26 (m, 2H), 7.15-6.80 (m, 5H), 6.05 (d, J=6 Hz, 1H), 5.22 (s, 2H), 5.16 (s, 2H) ES HRMS m/z 472.0033 (M+H C19H14F31NO2 requires 472.0018).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washThe organic solution was washed with a saturated solution of NaHCO3
  5. dry with materialbrine, dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash column chromatography (silica, eluent 90:10 methylene chloride/hexanes to 99:1 methylene chloride/methanol)

出典と根拠

ORDレコード
ord-5cabf8533a07426a86417a10cc136610
出典データセット
uspto-grants-2006_06
特許番号
US07067540B2

反応ノート

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