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

HRID 539116노트

반응식

HRID 539116 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c1ec90ce3acb4d9b99797f0dc8a25f3b
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865726B2

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