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1,2-Dibromoethane → HCID 57524148, 화합물

HRID 1477878
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HRID 1477878 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17]2)([CH2:14][CH3:15])[C:9](=[O:13])[CH2:10][C:11]#[N:12])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:33][CH2:34]Br>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([NH:25][S:26]([CH3:29])(=[O:27])=[O:28])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17]2)([C:9]2[O:13][CH2:33][CH2:34][C:10]=2[C:11]#[N:12])[CH2:14][CH3:15])=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 57524147HCID 57524147, 화합물

생성물 1

HCID 57524148HCID 57524148, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of N-(1-(3-(4-chlorophenyl)-1-cyano-2-oxopentan-3-yl)-1H-indol-4-yl)methanesulfonamide (50 mg, 0.116 mmol, enantiomer A), as described in Example 28 step A, in DMF (2 mL) was added NaH (9 mg, 0348 mmol, 60% in oil) at 0° C. After stirring for 30 min, 1,2-dibromoethane (22 mg, 0.116 mmol) was added to the mixture at 0° C. The resulting mixture was stirred at 0° C. for another 1 h, and then quenched with water (15 mL), extracted with ethyl acetate. The combined organic layers were washed with brine (10 mL), dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography eluting with PE/EA (5/1 to 3/1, v/v) to give the title compound as a colorless amorphous solid. LC/MS m/z=456.1[M+H]+.

후처리

  1. stirringThe resulting mixture was stirred at 0° C. for another 1 h
  2. customquenched with water (15 mL)
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with PE/EA (5/1 to 3/1

출처 및 근거

ORD 기록
ord-58b6277a174d4068a2d14a4bf0199912
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09403807B2

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