Iodine → HCID 178505447、化合物

HRID 246072ノート

反応式

HRID 246072 の反応式
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.[OH-].[K+].[I:13]I>CN(C=O)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([I:13])=[N:7][NH:8]2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 178423506-Fluoro-1H-indazole

生成物 1

HCID 178505447HCID 178505447、化合物収率 81.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 6-fluoro-1H-indazole (5.50 g, 40.4 mmol) in DMF (150 ml) at room temperature was added potassium hydroxide (6.8 g, 121 mmol) and iodine (15.4 g, 60.6 mmol). The maroon reaction mixture was stirred at room temperature for 8 h then quenched with 10% aqueous Na2S2O3 and diluted with water. The mixture was extracted with EtOAc (2×). The combined organics were washed with water, sat LiCl, and sat NaCl, then dried over MgSO4 and concentrated to afford 8.6 g (81%) of 6-fluoro-3-iodo-1H-indazole as a light yellow solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 7.48 (dd, J=8.9, 5.1 Hz, 1H), 7.20 (dd, J=8.9, 2.1 Hz, 1H), 7.02 (td, J=9.1, 2.1 Hz, 1H)

後処理

  1. customThe maroon reaction mixture
  2. customthen quenched with 10% aqueous Na2S2O3
  3. additiondiluted with water
  4. extractionThe mixture was extracted with EtOAc (2×)
  5. washThe combined organics were washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-64b729389bda463299c201a3d037ba5a
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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