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

HRID 1897503Notes

Reaction equation

HRID 1897503 reaction equation
[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

Participants

5

Reactant 3

HCID 14742,2'-Bipyridine2×HCID 4311764Sodium borohydride2×HCID 674094872-[5-(2-Cyano-4-fluorophenoxy)-indazol-1-yl]-N,N-dimethylacetamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5d141f52b6554292a06fe989efad7a00
Source dataset
uspto-grants-2013_08
Patent number
US08518983B2

Reaction notes

Loading…