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

HRID 2112208Notes

Reaction equation

HRID 2112208 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-e31e8ad7aadb4016b7f17b3a9a67a72b
Source dataset
uspto-grants-2009_04
Patent number
US07521447B2

Reaction notes

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