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N-bromobutanimide → 4-(6-Amino-5-bromopyridin-3-yl)-1-methylpyrrolidin-2-one

HRID 595925
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HRID 595925 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:12][N:11]([CH3:13])[C:10](=[O:14])[CH2:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Br:22])C(=O)C1.C(=O)(O)[O-].[Na+]>C(#N)C.CCOC(C)=O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:12][N:11]([CH3:13])[C:10](=[O:14])[CH2:9]2)=[CH:4][C:3]=1[Br:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 67184N-bromobutanimide2회HCID 516892Sodium BicarbonateHCID 1180470204-(6-Aminopyridin-3-yl)-1-methylpyrrolidin-2-one

생성물 1

HCID 1180455874-(6-Amino-5-bromopyridin-3-yl)-1-methylpyrrolidin-2-one

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857
Ethyl Acetate
용매

실험 절차

To 4-(6-aminopyridin-3-yl)-1-methylpyrrolidin-2-one (90 mg, 0.377 mmol) in Acetonitrile 3 mL) in ice bath was added NBS (60.3 mg, 0.339 mmol). The reaction mixture was stirred in ice bath for 15 min and room temperature for 30 min. LC-MS shows mixture of SM and product. Added 0.1 equiv. more of NBS and stirred another 1h at room temperature. Reaction mixture was diluted with EtOAc and added 2 mL of Satd sodium bicarbonate. Stirred 10 min. The organic layer was separated, dried over sodium sulfate, filtered and evaporated. Proceed for next step (73%). LCMS (m/z): 270.2/272.2 (MH+), 0.302 min.

후처리

  1. waitroom temperature for 30 min
  2. additionmixture of SM and product
  3. customReaction mixture
  4. stirringStirred 10 min
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. custom270.2/272.2 (MH+), 0.302 min.

출처 및 근거

ORD 기록
ord-2ce8528b38cf46b690634c6c82f7413d
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242996B2

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