7-Chlorothieno[3,2-b]pyridine → 2-(6-(1,3-Dioxan-2-yl)pyridin-3-yl)-7-chlorothieno[3,2-b]pyridine

HRID 1400897ノート

反応式

HRID 1400897 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][S:10][C:3]=12.[Li]CCCC.Br[C:17]1[CH:18]=[CH:19][C:20]([CH:23]2[O:28][CH2:27][CH2:26][CH2:25][O:24]2)=[N:21][CH:22]=1>C1COCC1.[Cl-].[Cl-].[Zn+2]>[O:24]1[CH2:25][CH2:26][CH2:27][O:28][CH:23]1[C:20]1[N:21]=[CH:22][C:17]([C:9]2[S:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH:8]=2)=[CH:18][CH:19]=1

参加物

6

反応物 3

HCID 112752517-Chlorothieno[3,2-b]pyridineHCID 584745645-Bromo-2-(1,3-dioxan-2-yl)pyridineHCID 178418339Butyllithium

生成物 1

HCID 584748922-(6-(1,3-Dioxan-2-yl)pyridin-3-yl)-7-chlorothieno[3,2-b]pyridine収率 59%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a stirred solution of 7-chlorothieno[3,2-b]pyridine (12.08 g, 71.2 mmol) in THF (138 mL) at −15° C. was added n-BuLi (30.7 mL, 77.0 mmol). After 30 min, a solution of ZnCl2 0.5 M in THF (142 mL, 71.2 mmol) was added at −15° C. and the reaction mixture was allowed to warm to RT over 45 min. A solution of palladium tetrakistriphenylphosphine (1.266 g, 1.096 mmol) and bromide 278 (13.37 g, 54.8 mmol) in THF (18.5 mL) was added and the mixture was heated to reflux for 2 h then concentrated. The residue was diluted with water and ammonium hydroxide and extracted with DCM. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was triturated with MTBE to afford the title compound 279 (10.70 g, 32.2 mmol, 59% yield) as light brown solid. MS (m/z): 333.33 (M+H).

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 h
  3. concentrationthen concentrated
  4. additionThe residue was diluted with water and ammonium hydroxide
  5. extractionextracted with DCM
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was triturated with MTBE

出典と根拠

ORDレコード
ord-d45fb2b9a1304b0fb4334e3338588d68
出典データセット
uspto-grants-2014_12
特許番号
US08906852B2

反応ノート

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