4-Methoxy[2,2′-bipyridine]-6-carbonitrile → HCID 67608342, compound

HRID 925287Notes

Reaction equation

HRID 925287 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]#[N:10])[N:6]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:4]=1>O1CCCC1.[Ni]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH2:10])[N:6]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:4]=1

Participants

4

Reactant 1

HCID 135867984-Methoxy[2,2′-bipyridine]-6-carbonitrile

Product 1

HCID 67608342HCID 67608342, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

Over a suspension of Ra—Ni (400 mg, excess) in tetrahydrofuran, under hydrogen, a solution of 4-Methoxy-[2,2′]bipyridinyl-6-carbonitrile (500 mg, 2.37 mmol) was added in tetrahydrofuran (10 mL) and the reaction mixture was stirred for 16 h at 25° C. The reaction was then filtered through celite, washed with tetrahydrofuran (100 mL) and the organic phase evaporated to dryness affording C-(4-Methoxy-[2,2′]bipyridinyl-6-yl)-methylamine as a pale yellow oil (466 mg, 91%).

Workup

  1. filtrationThe reaction was then filtered through celite
  2. washwashed with tetrahydrofuran (100 mL)
  3. customthe organic phase evaporated to dryness

Sources & evidence

ORD record
ord-ea10edc564fe4a58aba3d4b7491030fd
Source dataset
uspto-grants-2016_03
Patent number
US09284296B2

Reaction notes

Loading…