Sodium Hydroxide → 5-Iodo-2-(tetrahydro-pyran-4-yl)-pyridin-4-ylamine

HRID 917471ノート

反応式

HRID 917471 の反応式
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[C:11]([NH2:13])[CH:10]=[CH:9][N:8]=2)[CH2:3][CH2:2]1.[I:14]([O-])(=O)=O.[K+].[OH-].[Na+]>S(=O)(=O)(O)O>[I:14][C:10]1[C:11]([NH2:13])=[CH:12][C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[N:8][CH:9]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 23665710Potassium IodateHCID 589627052-(Oxan-4-yl)pyridin-4-amine

生成物 1

HCID 589627075-Iodo-2-(tetrahydro-pyran-4-yl)-pyridin-4-ylamine収率 27.1%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

実験手順

To a stirred solution of 5.80 g (32.5 mmol) 2-(tetrahydro-pyran-4-yl)-pyridin-4-ylamine in 20 ml 65% aqueous sulfuric acid heated to 135° C. was added 7.66 g (35.8 mmol) potassium iodate and stirring continued for 2.5 h at 135° C. The mixture was then cooled in an ice-bath before being made basic by addition of 5 N aqueous sodium hydroxide solution. The mixture was extracted three times with tetrahydrofuran and the combined organic phases were dried over sodium sulfate and concentrated in vacuo. The residue was resuspended in 200 ml tetrahydrofuran and 200 ml ethyl acetate and then concentrated in vacuo to 70 ml. The resulting crystals were collected by filtration to afford 2.68 g (27%) 5-iodo-2-(tetrahydro-pyran-4-yl)-pyridin-4-ylamine as a white crystalline solid. ES-MS m/e (%): 305 (M+H+, 100). The mother liquor was concentrated in vacuo; flash chromatography (methanol/dichloromethane 1/50 to 1/20) afforded a further 0.79 g (8%) 5-iodo-2-(tetrahydro-pyran-4-yl)-pyridin-4-ylamine as a white crystalline solid, as well as 0.98 g (10%) 3-iodo-2-(tetrahydro-pyran-4-yl)-pyridin-4-ylamine as a white crystalline solid. ES-MS m/e (%): 305 (M+H+, 100).

後処理

  1. temperatureThe mixture was then cooled in an ice-bath
  2. extractionThe mixture was extracted three times with tetrahydrofuran
  3. dry with materialthe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. concentration200 ml ethyl acetate and then concentrated in vacuo to 70 ml
  6. filtrationThe resulting crystals were collected by filtration

出典と根拠

ORDレコード
ord-51205c7099c548249bf975de822c992b
出典データセット
uspto-grants-2007_09
特許番号
US07273865B2

反応ノート

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