Dichloromethane → 6-Iodo-2,3-dimethoxypyridine

HRID 506770

反応式

HRID 506770 の反応式
C[O-].[Na+].Br[C:5]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]([I:13])[N:6]=1.[C:14]([O-])(O)=[O:15].[Na+].C(Cl)Cl>CN(C=O)C>[I:13][C:7]1[N:6]=[C:5]([O:15][CH3:14])[C:10]([O:11][CH3:12])=[CH:9][CH:8]=1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 110990402-Bromo-6-iodo-3-methoxypyridine2 回

生成物 1

HCID 453617466-Iodo-2,3-dimethoxypyridine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

Add NaOMe (1.4 equiv., 1.25 g, 23.14 mmol) to 2-bromo-6-iodo-3-methoxypyridine, 3 (4.95 g, 15.76 mmol) dissolved in DMF (10 mL), and stir the reaction medium, heating at 100° C. under N2 for 1 h. After cooling, the reaction mixture is shared between saturated NaHCO3 and CH2Cl2, and the organic phase is dried (MgSO4) and concentrated. Purification on SiO2 (EtOAc at 10%/heptane) gives 4 (3.13 g, 74.9% as a white solid: 1H NMR (CDCl3) δ 7.25 (d, 1H, J=7.8 Hz), 6.76 (d, 1H, J=8.1 Hz), 4.03 (s, 3H), 3.87 (s, 3H); m/z obs.=266 (M+1).

後処理

  1. temperatureAfter cooling
  2. dry with materialthe organic phase is dried (MgSO4)
  3. concentrationconcentrated
  4. customPurification on SiO2 (EtOAc at 10%/heptane)
  5. customgives 4 (3.13 g, 74.9% as a white solid

出典と根拠

ORDレコード
ord-d8b1f1068b584b6db9e9f9fc219aa174
出典データセット
uspto-grants-2010_08
特許番号
US07786114B2

関連ノート

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