tert-Butanol → HCID 57917443, 화합물

HRID 69145

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HRID 69145 반응식
[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

참가 물질

8

반응물 4

HCID 6386tert-ButanolHCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 57917482HCID 57917482, 화합물

생성물 1

HCID 57917443HCID 57917443, 화합물

시약·촉매·용매 3

HCID 23937Osmium촉매HCID 516892Sodium Bicarbonate용매HCID 218864351,4-Dioxane--water (1/1)용매

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온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0cef86927abf407b9d0afff550992f00
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822468B2

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