Cesium carbonate → Ethyl 3-(5-cyano-1H-indazol-1-yl)propanoate

HRID 2189778노트

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HRID 2189778 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>CN(C)C=O.CCOC(C)=O>[C:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[N:1]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:2]=[CH:3]2)#[N:11]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 68320Ethyl 3-bromopropionateHCID 111263841H-Indazole-5-carbonitrile

생성물 1

HCID 59316705Ethyl 3-(5-cyano-1H-indazol-1-yl)propanoate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

1H-indazole-5-carbonitrile (D1) (3.5 g, 24.45 mmol) was dissolved in N,N-dimethylformamide (60 ml). cesium carbonate (15.93 g, 48.9 mmol) and ethyl 3-bromopropanoate (4.68 ml, 36.7 mmol) were added. The mixture was heated at 80° C. for 4 hours. Diluted with EtOAc and washed with water (3×40 ml), dried over MgSO4 and evaporated. The mixture was purified by flash chromatography, eluting EtOAc/iso-Hexane 10-30% then 10-20% to give (3.682 g) for the first isomer (yellow oil) and (1.509 g) for the second isomer (pink solid). Analysis of the first isomer by 1H nmr indicated that is was the 1-isomer contaminated with the 2-isomer (ca. 20%) δH (d6-DMSO, 400 MHz) 1.05 (3H, t), 2.95 (2H, t), 3.97 (2H, q), 4.69 (2H, t), 7.74 (1H, dd), 7.92 (1H, dt), 8.28 (1H, d), 8.38 (1H, dd). MS (ES+): C13H13N3O2 requires 243; found (MH+) 244.

후처리

  1. washwashed with water (3×40 ml)
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe mixture was purified by flash chromatography
  5. washeluting EtOAc/iso-Hexane 10-30%
  6. custom10-20% to give (3.682 g) for the first isomer (yellow oil) and (1.509 g) for the second isomer (pink solid)

출처 및 근거

ORD 기록
ord-500a158a08024a3bb41f610e48df533d
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324254B2

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