Sodium hydride → (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(3-chlorophenyl)oxazolidin-2-one

HRID 539116ノート

反応式

HRID 539116 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:12][O:11][C:10](=[O:13])[NH:9]2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[Br:16][C:17]1[CH:18]=[N:19][N:20]2[CH:25]=[CH:24][C:23](Cl)=[N:22][C:21]=12.[Cl-].[NH4+]>CN(C=O)C>[Br:16][C:17]1[CH:18]=[N:19][N:20]2[CH:25]=[CH:24][C:23]([N:9]3[C@@H:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)[CH2:12][O:11][C:10]3=[O:13])=[N:22][C:21]=12

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 454805073-Bromo-5-chloropyrazolo(1,5-a)pyrimidineHCID 67033385(S)-4-(3-chlorophenyl)oxazolidin-2-one

生成物 1

HCID 67034388(S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(3-chlorophenyl)oxazolidin-2-one収率 45.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To (S)-4-(3-chlorophenyl)oxazolidin-2-one (278 mg, 1.41 mmol) in DMF (10 mL) was added sodium hydride (56.8 mg, 1.42 mmol) and the reaction was stirred at ambient temperature for 1 hour. 3-bromo-5-chloropyrazolo[1,5-a]pyrimidine (300 mg, 1.29 mmol) was added at once and the reaction was stirred at ambient temperature for 18 hours. Ice was added followed by ammonium chloride (aqueous), and the resulting suspension filtered and washed with water. After drying, (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(3-chlorophenyl)oxazolidin-2-one (231 mg, 45.5% yield) was isolated as a pale yellow solid.

後処理

  1. stirringwas stirred at ambient temperature for 18 hours
  2. additionIce was added
  3. filtrationthe resulting suspension filtered
  4. washwashed with water
  5. customAfter drying

出典と根拠

ORDレコード
ord-c1ec90ce3acb4d9b99797f0dc8a25f3b
出典データセット
uspto-grants-2014_10
特許番号
US08865726B2

反応ノート

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