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

HRID 2189777노트

반응식

HRID 2189777 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].ClCCC(OCC)=O>CN(C=O)C>[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 4

HCID 10796Cesium carbonateHCID 68320Ethyl 3-bromopropionateHCID 69341Ethyl 3-chloropropionateHCID 111263841H-Indazole-5-carbonitrile

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of 1H-indazole-5-carbonitrile (D1) (3.88 g, 27.3 mmol) in DMF (85 ml) was added Cs2CO3 (17.8 g, 54.6 mmol) and then ethyl 3-bromopropanoate (3.5 ml), 27 mmol) and ethyl 3-chloropropanoate (3.3 g, 24.2 mmol) were added. The reaction mixture was stirred at 80° C. for 4 hours and then allowed to cool. The solvent was removed in vacuo and the crude material was partitioned between EtOAc and water, the organics were separated, washed with brine, dried and evaporated. The crude was azeotroped with toluene and then purified by flash chromatography (EtOAc/hexane 1:9 to 1:1) to give 3.84 g of a yellow gum. MS data as for previous example.

후처리

  1. temperatureto cool
  2. customThe solvent was removed in vacuo
  3. customthe crude material was partitioned between EtOAc and water
  4. customthe organics were separated
  5. washwashed with brine
  6. customdried
  7. customevaporated
  8. customThe crude was azeotroped with toluene
  9. custompurified by flash chromatography (EtOAc/hexane 1:9 to 1:1)

출처 및 근거

ORD 기록
ord-97f1972c2270450ca4de36af76a67eca
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324254B2

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