Tetrahydrofuran → 1-[3-Fluoro-4-(2,2,2-trifluoro-1-hydroxy-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80263

반응식

HRID 80263 반응식
C[Si](C)(C)[C:3]([F:6])([F:5])[F:4].C1COCC1.C([O-])([O-])=O.[K+].[K+].[F:20][C:21]1[CH:28]=[C:27]([N:29]2[CH2:33][CH2:32][N:31]([C:34]3[CH:35]=[N:36][CH:37]=[CH:38][C:39]=3[CH3:40])[C:30]2=[O:41])[CH:26]=[CH:25][C:22]=1[CH:23]=[O:24]>CN(C=O)C.C(Cl)(Cl)Cl.CO>[F:20][C:21]1[CH:28]=[C:27]([N:29]2[CH2:33][CH2:32][N:31]([C:34]3[CH:35]=[N:36][CH:37]=[CH:38][C:39]=3[CH3:40])[C:30]2=[O:41])[CH:26]=[CH:25][C:22]=1[CH:23]([OH:24])[C:3]([F:6])([F:5])[F:4]

참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 596361642-Fluoro-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde

생성물 1

HCID 596362271-[3-Fluoro-4-(2,2,2-trifluoro-1-hydroxy-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one수율 65.92%

시약·촉매·용매 3

HCID 887Methanol용매HCID 6212Chloroform용매HCID 6228Dimethylformamide용매

실험 절차

0.5M solution of trimethyl-trifluoromethyl-silane in THF (6.68 mL, 3.344 mmol) and K2CO3 (250 mg, 10.82 mmol) were added to 2-fluoro-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde (I-121a: 400 mg, 1.337 mmol) in dry DMF (5 mL) under nitrogen atmosphere. The resulting mixture was stirred at room temperature overnight. The reaction was monitored by TLC (5% MeOH in CHCl3). The reaction mixture was quenched with brine solution and the THF layer was concentrated. The aqueous layer was extracted with chloroform. The organic layer was dried over Na2SO4 and concentrated to get the crude product. Purification by column chromatography on silica gel (2.5% MeOH in CHCl3), followed by hexane wash, afforded 325 mg of the product (65.92% yield).

후처리

  1. customThe reaction mixture was quenched with brine solution
  2. concentrationthe THF layer was concentrated
  3. extractionThe aqueous layer was extracted with chloroform
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customto get the crude product
  7. customPurification by column chromatography on silica gel (2.5% MeOH in CHCl3)
  8. washwash

출처 및 근거

ORD 기록
ord-0faa4661d1c040959a9c95552cc9bdd9
출처 데이터셋
uspto-grants-2014_09
특허 번호
USRE045173E1

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