2,2'-Bipyridine → 2-[5-(2-Aminomethyl-4-fluorophenoxy)-indazol-1-yl]-N,N-dimethylacetamide

HRID 1897503노트

반응식

HRID 1897503 반응식
[C:1]([C:3]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:4]=1[O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[N:10]=[CH:9]2)#[N:2].N1C=CC=CC=1C1C=CC=CN=1.[BH4-].[Na+]>CCO>[NH2:2][CH2:1][C:3]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:4]=1[O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[N:10]=[CH:9]2

참가 물질

5

반응물 3

HCID 14742,2'-Bipyridine2회HCID 4311764Sodium borohydride2회HCID 674094872-[5-(2-Cyano-4-fluorophenoxy)-indazol-1-yl]-N,N-dimethylacetamide

생성물 1

HCID 674102372-[5-(2-Aminomethyl-4-fluorophenoxy)-indazol-1-yl]-N,N-dimethylacetamide수율 11%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 2-[5-(2-cyano-4-fluorophenoxy)-indazol-1-yl]-N,N-dimethylacetamide (0.090 g, 0.266 mmol) in EtOH (0.5 mL) was added CoBr2 (27 μL, 0.005 mmol) followed by [2,2′]bipyridinyl (81 μL, 0.015 mmol). NaBH4 (0.030 g, 0.798 mmol) was added to the mixture and it was stirred at room temperature for 18 hours. The mixture was treated with another portion each of CoBr2, [2,2′]bipyridinyl, and NaBH4 and stirred for another 18 hours. The mixture was quenched with MeOH, followed by acetic acid and then concentrated under reduced pressure. The white residue was partitioned between saturated NaHCO3 and ethyl acetate. The organic layer was filtered and concentrated under reduced pressure to afford 10 mg of white solid (11% yield).

후처리

  1. stirringstirred for another 18 hours
  2. customThe mixture was quenched with MeOH
  3. concentrationconcentrated under reduced pressure
  4. customThe white residue was partitioned between saturated NaHCO3 and ethyl acetate
  5. filtrationThe organic layer was filtered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5d141f52b6554292a06fe989efad7a00
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518983B2

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