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

HRID 245874ノート

反応式

HRID 245874 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-13c85eb8bfd543448abf04ec99743112
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

反応ノート

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