Methyl iodide → 4-Fluoro-N-methyl-N-[2-(5-methyl-furan-2-yl)-ethyl]-benzamide

HRID 1441809

반응식

HRID 1441809 반응식
[H-].[Na+].[F:3][C:4]1[CH:20]=[CH:19][C:7]([C:8]([NH:10][CH2:11][CH2:12][C:13]2[O:14][C:15]([CH3:18])=[CH:16][CH:17]=2)=[O:9])=[CH:6][CH:5]=1.I[CH3:22]>C1COCC1>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]([CH3:22])[CH2:11][CH2:12][C:13]2[O:14][C:15]([CH3:18])=[CH:16][CH:17]=2)=[O:9])=[CH:19][CH:20]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 218748464-Fluoro-N-[2-(5-methyl-2-furanyl)ethyl]benzamide

생성물 1

HCID 218749624-Fluoro-N-methyl-N-[2-(5-methyl-furan-2-yl)-ethyl]-benzamide수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

NaH (60% dispersion in oil, 65 mg, 1.63 mmol) was added portionwise to a solution of 4-fluoro-N-[2-(5-methyl-2-furanyl)ethyl]benzamide (269 mg, 1.09 mmol, 237A) in THF (5 mL). After gas evolution ceased, iodomethane (0.14 mL, 2.18 mmol) was added drop-wise. Once HPLC analysis showed the reaction to be 50% complete, the mixture was concentrated under reduced pressure and resubjected to the above conditions. After all the starting material was consumed, H2O was added and the resulting mixture was extracted with EtOAc (2×5 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography on silica gel eluting with 20% acetone/CHCl3 gave 238 mg (84%) of compound 425A. HPLC: 98% at 2.94 min (retention time) (Phenomenex-prime S5-C18 column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z [M+H]=262.38.

후처리

  1. customthe reaction
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customAfter all the starting material was consumed
  4. additionH2O was added
  5. extractionthe resulting mixture was extracted with EtOAc (2×5 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash chromatography on silica gel eluting with 20% acetone/CHCl3

출처 및 근거

ORD 기록
ord-a73211888a1c4dfa9c630de66296a1af
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07655689B2

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