Ammonium Chloride → 1-Azido-2-(2-bromo-5-fluoro-pyridin-4-yl)-propan-2-ol

HRID 474081ノート

反応式

HRID 474081 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([OH:16])([CH3:15])[CH2:9]OS(C)(=O)=O)[C:5]([F:17])=[CH:4][N:3]=1.[N-:18]=[N+:19]=[N-:20].[Na+].[NH4+].[Cl-]>C(O)C.O.CC(OC)(C)C>[N:18]([CH2:9][C:8]([C:6]1[C:5]([F:17])=[CH:4][N:3]=[C:2]([Br:1])[CH:7]=1)([OH:16])[CH3:15])=[N+:19]=[N-:20]

参加物

7

反応物 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 86668051Methanesulfonic acid 2-(2-bromo-5-fluoro-pyridin-4-yl)-2-hydroxy-propyl ester

生成物 1

HCID 866680521-Azido-2-(2-bromo-5-fluoro-pyridin-4-yl)-propan-2-ol

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 15413tert-Butyl methyl ether溶媒

反応条件

温度
80 °C

実験手順

To a solution of methanesulfonic acid 2-(2-bromo-5-fluoro-pyridin-4-yl)-2-hydroxy-propyl ester (10.36 g, 31.6 mmol) in ethanol (160 ml) was added NaN3 (5.13 g, 79.0 mmol) and NH4Cl (8.44 g, 158.0 mmol). The reaction mixture was stirred at 80° C. for 20 h. The reaction mixture was diluted with H2O and TBME and the phases were separated. The aq. phase was twice reextracted with TBME, the combined org. phases were washed with brine, dried over Na2SO4, filtered and concentrated. HPLC RtH4=0.89 min; ESIMS: 275, 277 [(M+H)+]; 1H NMR (400 MHz, CDCl3): δ 8.20 (d, 1H), 7.80 (d, 1H), 3.81 (d, 1H), 3.65 (d, 1H), 1.61 (s, 3H).

後処理

  1. customthe phases were separated
  2. washphases were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customHPLC RtH4=0.89 min

出典と根拠

ORDレコード
ord-7e4a85788f3f4f4694d1651d59b1eb78
出典データセット
uspto-grants-2014_01
特許番号
US08637508B2

反応ノート

読み込み中…