Sodium Azide → 4-Azido-6-bromo-2-chloro-3-(difluoromethoxy)pyridine

HRID 407217

反応式

HRID 407217 の反応式
Br[C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([Cl:9])[C:3]=1[O:10][CH:11]([F:13])[F:12].[N-:14]=[N+:15]=[N-:16].[Na+]>CN(C=O)C>[N:14]([C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([Cl:9])[C:3]=1[O:10][CH:11]([F:13])[F:12])=[N+:15]=[N-:16]

参加物

4

反応物 2

HCID 33557Sodium AzideHCID 86675402HCID 86675402、化合物

生成物 1

HCID 866754034-Azido-6-bromo-2-chloro-3-(difluoromethoxy)pyridine収率 48.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

4,6-Dibromo-2-chloro-3-(difluoromethoxy)pyridine (780 mg, 2.312 mmol) was dissolved in DMF (5 mL), and sodium azide (180 mg, 2.77 mmol) was added. The reaction mixture was heated at 65° C. for 2 h and the progress of the reaction was checked by liquid chromatography-mass spectrometry (LC-MS). The reaction appeared to be mostly complete. The product was partitioned between Et2O and H2O. The aqueous phase was then extracted twice more with Et2O. The organic extracts were combined, diluted with petroleum ether, washed twice with H2O, dried, and concentrated. The product was purified by column chromatography (SiO2, EtOAc/hexane gradient) to yield 4-azido-6-bromo-2-chloro-3-(difluoromethoxy)-pyridine (0.335 g, 48.4%): 1H NMR (300 MHz, CDCl3) δ 7.26 (s, 1H), 6.59 (t, J=73.6, 1H).

後処理

  1. customThe product was partitioned between Et2O and H2O
  2. extractionThe aqueous phase was then extracted twice more with Et2O
  3. additiondiluted with petroleum ether
  4. washwashed twice with H2O
  5. customdried
  6. concentrationconcentrated
  7. customThe product was purified by column chromatography (SiO2, EtOAc/hexane gradient)

出典と根拠

ORDレコード
ord-936a03b1ed174943acf86b9cf6c1e710
出典データセット
uspto-grants-2014_06
特許番号
US08754229B2

関連ノート

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