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

HRID 80206

反応式

HRID 80206 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒

実験手順

A 0.5M solution of trimethyl-trifluoromethyl-silane in THF (6.68 mL, 3.344 mmol) and K2CO3 (250 mg, 10.82 mmol) was 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 thin layer chromatography (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).

後処理

  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

出典と根拠

ORDレコード
ord-8cda949c77e44c26bc4ebcbb03d0e4d6
出典データセット
uspto-grants-2014_09
特許番号
USRE045173E1

関連ノート

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