Iodine → HCID 71279920、化合物

HRID 246345ノート

反応式

HRID 246345 の反応式
[CH:1]1[N:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(=O)(O)[O-].[Na+].[I:15]I>CCO.O>[I:15][C:1]1[N:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

参加物

6

反応物 3

HCID 807IodineHCID 274090Imidazo(1,5-a)pyridineHCID 516892Sodium Bicarbonate

生成物 1

HCID 71279920HCID 71279920、化合物収率 63%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a solution of imidazo[1,5-a]pyridine (0.50 g, 4.23 mmol) in EtOH (8 mL) and water (4 mL) was added sodium bicarbonate (1.07 g, 12.7 mmol) followed by iodine (1.61 g, 6.35 mmol). The dark maroon-brown heterogeneous reaction mixture was stirred at room temperature overnight then quenched with aqueous 10% Na2S2O3, diluted with water and extracted with EtOAc (3×). The combined organics were washed with water, dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography with 20% to 50% EtOAc/hexanes to afford 649 mg (63%) of 1-iodo-imidazo[1,5-a]pyridine as a light brown solid (light sensitive). 1H NMR (CDCl3, 300 MHz): δ (ppm) 8.13 (s, 1H), 7.92 (d, J=6.8 Hz, 1H), 7.33 (d, J=9.4 Hz, 1H), 6.80 (dd, J=9.4, 6.8 Hz, 1H), 6.56-6.69 (m, 1H).

後処理

  1. customthen quenched with aqueous 10% Na2S2O3
  2. additiondiluted with water
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organics were washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography with 20% to 50% EtOAc/hexanes

出典と根拠

ORDレコード
ord-307e2fbf3d7141c1a84e2ad232cbaab9
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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