Potassium Carbonate → HCID 59401866、化合物

HRID 391176ノート

反応式

HRID 391176 の反応式
Cl.[CH3:2][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH:8]1[CH2:12][CH2:11][NH:10][CH2:9]1.F[C:14]1[CH:15]=[CH:16][C:17]([N+:21]([O-:23])=[O:22])=[C:18]([CH3:20])[CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:2][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH:8]1[CH2:12][CH2:11][N:10]([C:14]2[CH:15]=[CH:16][C:17]([N+:21]([O-:23])=[O:22])=[C:18]([CH3:20])[CH:19]=2)[CH2:9]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 949565-Fluoro-2-nitrotolueneHCID 666245402-Methyl-[1,3']bipyrrolidinyl hydrochloride2 回

生成物 1

HCID 59401866HCID 59401866、化合物

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
85 °C

実験手順

2-Methyl-[1,3′]bipyrrolidinyl hydrochloride (Intermediate (ii) obtained above, 5.3 g, 21.6 mmol, 1.12 equiv.) was dissolved in anhydrous DMSO (30 mL). To this solution was added 5-fluoro-2-nitrotoluene (3.00 g, 18.78 mmol, 1 equiv.), followed by powdered potassium carbonate (8.9 g, 65 mmol). The suspension was heated on an oil bath to 85° C. for 4 h when the starting material was consumed as determined by TLC (5% MeOH in DCM) and LC/MS. To the suspension were added 20 mL of water and 50 mL of DCM. The two layers were separated, and the aqueous layer was extracted with DCM (20 mL×2). The combined DCM extracts were washed with sodium bicarbonate (20 mL), and brine (15 mL×2), dried (anhydrous potassium carbonate), filtered, and concentrated in vacuo. The crude product was purified on a silica gel column, eluted with 5% MeOH in DCM to get the title compound as a yellow solid after drying, 5.47 g (100%). MS: 290 (M+H+).

後処理

  1. customwas consumed
  2. additionTo the suspension were added 20 mL of water and 50 mL of DCM
  3. customThe two layers were separated
  4. extractionthe aqueous layer was extracted with DCM (20 mL×2)
  5. washThe combined DCM extracts were washed with sodium bicarbonate (20 mL), and brine (15 mL×2)
  6. dry with materialdried (anhydrous potassium carbonate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified on a silica gel column
  10. washeluted with 5% MeOH in DCM

出典と根拠

ORDレコード
ord-877925d8e2ab4b44a45319595b832009
出典データセット
uspto-grants-2013_02
特許番号
US08383814B2

反応ノート

読み込み中…