Iodine → 3-Iodo-5-phenylsulfanyl-1H-pyrrolo[2,3-b]pyridine

HRID 1991094ノート

反応式

HRID 1991094 の反応式
[C:1]1([S:7][C:8]2[CH:9]=[C:10]3[CH:16]=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[I:19]I.[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C.O>[I:19][C:16]1[C:10]2[C:11](=[N:12][CH:13]=[C:8]([S:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:9]=2)[NH:14][CH:15]=1

参加物

7

反応物 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 591287095-Phenylsulfanyl-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 591287053-Iodo-5-phenylsulfanyl-1H-pyrrolo[2,3-b]pyridine収率 98%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2 (135 mg, 0.60 mmol) in DMF (1.5 mL) was added solid KOH (124 mg, 2.21 mmol) and the reaction mixture stirred for 20 min. Iodine (167 mg, 0.66 mmol) was then added and the stirring continued for 40 min. A mixture of water (8.8 mL) and sat. aq. Na2S2O3 (1.3 mL) was added rapidly, and the resulting solid filtered off, washed with water (2×) and dried in vacuum to give iodide 3 as a creamy solid (205 mg, 98%); 1H NMR (400 MHz, CDCl3+2 drops CD3OD) δ 7.10-7.30 (m, 5H), 7.45 (s, 1H), 7.94 (d, J=2.0 Hz, 1H), 8.35 (d, J=1.9 Hz, 1H).

後処理

  1. waitthe stirring continued for 40 min
  2. additionwas added rapidly
  3. filtrationthe resulting solid filtered off
  4. washwashed with water (2×)
  5. customdried in vacuum

出典と根拠

ORDレコード
ord-333e844165204f2bb43227c41999f2f3
出典データセット
uspto-grants-2010_01
特許番号
US07645769B2

反応ノート

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