Methanol → 1-[4-(Cyclopropyl-hydroxy-methyl)-3-fluoro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80208

反応式

HRID 80208 の反応式
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[F:6][C:7]1[CH:14]=[C:13]([N:15]2[CH2:19][CH2:18][N:17]([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][C:25]=3[CH3:26])[C:16]2=[O:27])[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10].CO>C1COCC1.C(Cl)(Cl)Cl>[CH:1]1([CH:9]([OH:10])[C:8]2[CH:11]=[CH:12][C:13]([N:15]3[CH2:19][CH2:18][N:17]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][C:25]=4[CH3:26])[C:16]3=[O:27])=[CH:14][C:7]=2[F:6])[CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 887MethanolHCID 596361642-Fluoro-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehydeHCID 178418630HCID 178418630、化合物

生成物 1

HCID 596361411-[4-(Cyclopropyl-hydroxy-methyl)-3-fluoro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one収率 99.41%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A 0.5M solution of cyclopropyl magnesium bromide in THF (2.4 mL, 1.170 mmol) was added dropwise to 2-fluoro-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde (I-121a: 175 mg, 0.585 mmol) in dry THF (10 mL) at 0° C. under nitrogen atmosphere. The resulting mixture was stirred at room temperature for 3 hours. The reaction was monitored by TLC (5% MeOH in CHCl3). The reaction mixture was quenched with aqueous NH4Cl solution and the THF layer was concentrated. The aqueous layer was extracted with ethylacetate. The organic layer was dried over Na2SO4 and concentrated to afford the crude product. Purification by column chromatography on silica gel (3% MeOH in CHCl3), followed by hexane wash, afforded 200 mg of the product (99.41% yield).

後処理

  1. customThe reaction mixture was quenched with aqueous NH4Cl solution
  2. concentrationthe THF layer was concentrated
  3. extractionThe aqueous layer was extracted with ethylacetate
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customto afford the crude product
  7. customPurification by column chromatography on silica gel (3% MeOH in CHCl3)
  8. washwash

出典と根拠

ORDレコード
ord-c323f36ffc3a460b8657f46c3124e82d
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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