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

HRID 2246006노트

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HRID 2246006 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3d31a406a2e0488990f0c78740231510
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687052B2

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