Iodine → 6-Fluoro-1-iodo-3-methylsulfanyl-imidazo[1,5-a]pyridine

HRID 245874노트

반응식

HRID 245874 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([S:11][CH3:12])=[N:9][CH:10]=2)[CH:7]=1.O.C(=O)(O)[O-].[Na+].[I:19]I>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([S:11][CH3:12])=[N:9][C:10]=2[I:19])[CH:7]=1

참가 물질

6

반응물 4

HCID 807IodineHCID 962WaterHCID 516892Sodium BicarbonateHCID 866779116-Fluoro-3-methylsulfanyl-imidazo[1,5-a]pyridine

생성물 1

HCID 712803106-Fluoro-1-iodo-3-methylsulfanyl-imidazo[1,5-a]pyridine수율 41%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

In a round-bottomed flask, 6-fluoro-3-methylsulfanyl-imidazo[1,5-a]pyridine (178 mg, 0.88 mmol) was dissolved in ethanol (1.6 ml). Water (0.8 ml), sodium bicarbonate (278 mg, 3.31 mmol) and iodine (312 mg, 1.23 mmol) were added. The dark brown suspension was stirred at room temperature overnight then quenched with 10% aqueous Na2S2O3 and extracted with EtOAc (2×). The combined organic layers were washed with 10% aqueous Na2S2O3, water, and brine then dried over sodium sulfate, filtered and concentrated. The residue was absorbed on silica gel and chromatographed with EtOAc/hexanes (gradient 0-10% EtOAc) to afford 110 mg (41%) of 6-fluoro-1-iodo-3-methylsulfanyl-imidazo[1,5-a]pyridine as a brown solid.

후처리

  1. customthen quenched with 10% aqueous Na2S2O3
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with 10% aqueous Na2S2O3, water, and brine
  4. dry with materialthen dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was absorbed on silica gel
  8. customchromatographed with EtOAc/hexanes (gradient 0-10% EtOAc)

출처 및 근거

ORD 기록
ord-13c85eb8bfd543448abf04ec99743112
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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