Sodium borohydride → 6-Bromo-2-chloro-3-(difluoromethoxy)pyridin-4-amine

HRID 407218

反応式

HRID 407218 の反応式
[N:1]([C:4]1[CH:9]=[C:8]([Br:10])[N:7]=[C:6]([Cl:11])[C:5]=1[O:12][CH:13]([F:15])[F:14])=[N+]=[N-].[BH4-].[Na+]>CO>[Br:10][C:8]1[N:7]=[C:6]([Cl:11])[C:5]([O:12][CH:13]([F:15])[F:14])=[C:4]([NH2:1])[CH:9]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 866754034-Azido-6-bromo-2-chloro-3-(difluoromethoxy)pyridine

生成物 1

HCID 866754046-Bromo-2-chloro-3-(difluoromethoxy)pyridin-4-amine収率 77.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

4-Azido-6-bromo-2-chloro-3-(difluoromethoxy)pyridine (0.563 g, 1.880 mmol) was then dissolved in CH3OH (15 mL), and NaBH4 (0.107 g, 2.82 mmol) was added. The reaction mixture was stirred at ambient temperature for 15 min at which point thin-layer chromatographic (TLC) analysis indicated complete consumption of starting material. The reaction mixture was concentrated and partitioned between EtOAc and H2O. The organic phase was dried and concentrated. The product was purified by flash chromatography (SiO2, EtOAc/hexane gradient) to yield the title compound as a white solid (0.398 g, 77%): mp 138-140° C.; 1H NMR (600 MHz, DMSO-d6) δ 6.98 (t, J=73.1 Hz, 1H), 6.84 (d, J=14.6 Hz, 2H); EIMS m/z 274.

後処理

  1. customconsumption of starting material
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between EtOAc and H2O
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customThe product was purified by flash chromatography (SiO2, EtOAc/hexane gradient)

出典と根拠

ORDレコード
ord-2f0be027e79b4c5b84b5ffdb7dc6833e
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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