Iodine → HCID 71279920, 화합물

HRID 246345노트

반응식

HRID 246345 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 71279920HCID 71279920, 화합물수율 63%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-307e2fbf3d7141c1a84e2ad232cbaab9
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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