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

HRID 917471노트

반응식

HRID 917471 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-51205c7099c548249bf975de822c992b
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07273865B2

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