tert-Butanol → HCID 57917443、化合物

HRID 69145

反応式

HRID 69145 の反応式
[F:1][C:2]1[C:7]([CH:8]=C)=[CH:6][N:5]2[CH:10]=[CH:11][N:12]=[C:4]2[CH:3]=1.I([O-])(=O)(=O)=[O:14].[Na+].N1C(C)=CC=CC=1C.C(O)(C)(C)C>O1CCOCC1.O.C([O-])(O)=O.[Na+].[Os]>[F:1][C:2]1[C:7]([CH:8]=[O:14])=[CH:6][N:5]2[CH:10]=[CH:11][N:12]=[C:4]2[CH:3]=1

参加物

8

反応物 4

HCID 6386tert-ButanolHCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 57917482HCID 57917482、化合物

生成物 1

HCID 57917443HCID 57917443、化合物

試薬・触媒・溶媒 3

HCID 23937Osmium触媒HCID 516892Sodium Bicarbonate溶媒HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
50 °C

実験手順

To 7-fluoro-6-vinyl-imidazo[1,2-a]pyridine (xv) (94 mg, 0.58 mmol), sodium periodate (496 mg, 2.32 mmol) and 2,6-lutidine (0.135 mL, 1.16 mmol) in dioxane/water 3:1 (4.8 mL) was added in two portions a 2.5% solution of osmium tetroxyde in tert-butanol (2×0.728 mL, 2×0.058 mmol). The RM was stirred at rt for 19.5 h and at 50° C. for 24 h. The RM was diluted with aqueous saturated NaHCO3 and extracted twice with EtOAc. The organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by chromatography with DCM and MeOH to yield the title product as a brown solid (TLC RF (DCM/MeOH 9: 1)=0.40, MH+=165).

後処理

  1. extractionextracted twice with EtOAc
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by chromatography with DCM and MeOH

出典と根拠

ORDレコード
ord-0cef86927abf407b9d0afff550992f00
出典データセット
uspto-grants-2014_09
特許番号
US08822468B2

関連ノート

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