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Phenethyl bromide → HCID 89862978, 화합물

HRID 1053682
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인쇄 미리보기

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HRID 1053682 반응식
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:7]=[C:8]([C@H:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])[CH:9]=[CH:10][CH:11]=2)[CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(#N)C.CN(C=O)C>[CH2:29]([N:1]1[CH:5]=[C:4]([C:6]2[CH:7]=[C:8]([C@H:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])[CH:9]=[CH:10][CH:11]=2)[CH:3]=[N:2]1)[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 89862967HCID 89862967, 화합물

생성물 1

HCID 89862978HCID 89862978, 화합물수율 77.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

To a vial was added Intermediate 11B (110 mg, 0.383 mmol) in acetonitrile (0.7 mL) and DMF (0.7 mL) and potassium carbonate (159.0 mg, 1.148 mmol). The reaction was stirred for 10 min before (2-bromoethyl)benzene (106 mg, 0.574 mmol) was added. The resulting mixture was heated at 50° C. for 16 h. The reaction was quenched with water and extracted with EtOAc. The combined organics were dried over Na2SO4 and concentrated. The crude was purified by flash chromatography to give Intermediate 11C (116 mg, 0.296 mmol, 77.0% yield) as a white solid. LCMS=2.20 min [M+1]=392.3 (Method B).

후처리

  1. additionwas added
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organics were dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude was purified by flash chromatography

출처 및 근거

ORD 기록
ord-b51552c452614acea6762c15eda9f815
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09394260B2

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