Formaldehyde → 4-[(E)-2-[6-[2-[2-(2-fluoroethoxy)ethoxy]ethoxy]pyridin-3-yl]ethenyl]-N-methylaniline

HRID 2246006ノート

反応式

HRID 2246006 の反応式
[CH3:1][O-].[Na+].[F:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]2[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=2)=[CH:16][N:15]=1.C=O.[BH4-].[Na+]>CO.O.ClCCl>[F:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]2[CH:27]=[CH:26][C:25]([NH:28][CH3:1])=[CH:24][CH:23]=2)=[CH:16][N:15]=1

参加物

8

反応物 4

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 86618271(E)-2-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-5-(4-aminostyryl)pyridine

生成物 1

HCID 573968654-[(E)-2-[6-[2-[2-(2-fluoroethoxy)ethoxy]ethoxy]pyridin-3-yl]ethenyl]-N-methylaniline収率 73%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Sodium methoxide (1M in methanol, 0.23 ml) was added to a solution of compound 5 (15.8 mg, 0.046 mmol) in methanol (5 ml) followed by the addition of paraformaldehyde (6.6 mg, 0.23 mmol). The reaction mixture was refluxed for 1.5 hour then cooled to 0° C. with an ice bath. Sodium borohydride (10.4 mg, 0.27 mmol) was added with caution. The mixture was refluxed again for 1 hour and cooled down. Dichloromethane and water was added. Organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by PTLC (3% MeOH in DCM as developing solvent) to give product 6 (12 mg, Yield: 73%): 1H NMR (200 MHz, CDCl3): δ.8.14 (1H, d, J=2.2 Hz), 7.76 (1H, d, d, J=8.6 Hz, J2=2.4 Hz), 7.35 (2H, d, J=8.6 Hz), 6.92 (1H, d, J=16.4 Hz), 6.80 (1H, d, J=16.4 Hz), 6.76 (2H, d, J=8.6 Hz), 4.53 (2H, d, t, J1=47.6 Hz, J2=4.2 Hz), 4.49 (2H, t, J=4.8 Hz), 3.85 (3H, m), 3.70 (5H, m), 2.88 (3H, s). HRMS (EI) m/z calcd. for [C20H25FN2O3]+ 360.1849.

後処理

  1. temperatureThe reaction mixture was refluxed for 1.5 hour
  2. temperatureThe mixture was refluxed again for 1 hour
  3. temperaturecooled down
  4. customOrganic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated
  8. customThe residue was purified by PTLC (3% MeOH in DCM as developing solvent)

出典と根拠

ORDレコード
ord-3d31a406a2e0488990f0c78740231510
出典データセット
uspto-grants-2010_03
特許番号
US07687052B2

反応ノート

読み込み中…