Sodium Hydroxide → 3-azido-6-bromo-9H-carbazole

HRID 62164

반응식

HRID 62164 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10](Br)=[CH:9][CH:8]=3.[N-:16]=[N+:17]=[N-:18].[Na+].N1CCC[C@H]1C(O)=O.[OH-].[Na+]>CCO.O.[Cu]I>[N:16]([C:10]1[CH:9]=[CH:8][C:7]2[NH:6][C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([Br:1])=[CH:3][CH:4]=3)=[N+:17]=[N-:18]

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 145742L-ProlineHCID 2748743,6-Dibromocarbazole

생성물 1

HCID 580658773-azido-6-bromo-9H-carbazole

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 19096565Water ethanol용매

반응 조건

온도
95 °C

실험 절차

3,6-Dibromocarbazole (0.500 g, 1.538 mmol), NaN3 (0.120 g, 1.846 mmol), CuI (0.029 g, 0.154 mmol), L-proline (0.053 g, 0.461 mmol) and NaOH (0.019 g, 0.461 mmol) were dissolved in 7:3 EtOH/H2O (3.0 mL) and heated to 95° C. under a N2 atmosphere for 24 h. The completed reaction was partitioned between EtOAc/H2O (3×) and the combined organics were washed with satd. aq. NaCl, dried over Na2SO4, filtered, and concentrated. The crude residue was purified by chromatography (SiO2, 0-15% EtOAc/toluene), followed by HPLC (Phenomenex SiO2 Luna 10 μ, 250×21.2 mm column, 50% EtOAc/Hexane, 21 mL/min, retention time=48 min) to afford the desired product.

후처리

  1. customThe completed reaction
  2. customwas partitioned between EtOAc/H2O (3×)
  3. washthe combined organics were washed with satd
  4. dry with materialaq. NaCl, dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by chromatography (SiO2, 0-15% EtOAc/toluene)

출처 및 근거

ORD 기록
ord-8b6b2c436a844a6fa102277dd7b1d20f
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09446022B2

연결된 노트

불러오는 중…