Sodium Iodide → HCID 57658448、化合物

HRID 1667363ノート

反応式

HRID 1667363 の反応式
[NH2:1][C:2]1[N:7]([C:8]2[C:13]([F:14])=[CH:12][C:11]([OH:15])=[CH:10][C:9]=2[F:16])[C:6](=[O:17])[CH:5]=[CH:4][C:3]=1[C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=1[F:26].Br[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][Cl:34].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].NC1N(C2C(F)=CC(OCCCCCI)=CC=2F)C(=O)C=CC=1C(=O)C1C=CC(F)=CC=1F>CC(C)=O>[NH2:1][C:2]1[N:7]([C:8]2[C:9]([F:16])=[CH:10][C:11]([O:15][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][Cl:34])=[CH:12][C:13]=2[F:14])[C:6](=[O:17])[CH:5]=[CH:4][C:3]=1[C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=1[F:26]

参加物

7

反応物 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 960701-Bromo-5-chloropentaneHCID 58608543HCID 58608543、化合物HCID 67444810HCID 67444810、化合物

生成物 1

HCID 57658448HCID 57658448、化合物

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
70 °C

実験手順

To a solution of 6-amino-5-(2,4-difluorobenzoyl)-1-(2,6-difluoro-4-hydroxyphenyl)-pyridin-2(1H)-one (300 mg, 0.79 mmol) in acetone (6 ml) under an atmosphere of nitrogen was added 1-bromo-5-chloropentane (0.115 ml, 0.87 mmol, 1.1 eq), sodium iodide (238 mg, 1.59 mmol, 2 eq) and potassium carbonate (438 mg, 3.17 mmol, 4 eq). The mixture was heated at 70° C. for 16 hours, before being allowed to cool to room temperature and partitioned between EtOAc (50 ml) and water (50 ml). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. Purification by column chromatography (30% EtOAc in heptane) afforded a 3:2 mixture of the title compound and 6-amino-1-{4-[(5-iodopentyl)oxy]-2,6-difluorophenyl}-5-(2,4-difluorobenzoyl)pyridin-2(1H)-one (142 mg) which was used without further purification.

後処理

  1. temperatureto cool to room temperature
  2. custompartitioned between EtOAc (50 ml) and water (50 ml)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by column chromatography (30% EtOAc in heptane)
  7. customafforded

出典と根拠

ORDレコード
ord-b327cb246d3f4045a608e75bf0fba842
出典データセット
uspto-grants-2011_10
特許番号
US08044211B2

反応ノート

読み込み中…