N-bromobutanimide → HCID 118045721, compound

HRID 595845Notes

Reaction equation

HRID 595845 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[N:10][C:11]([NH2:14])=[CH:12][CH:13]=1.C1C(=O)N([Br:22])C(=O)C1>C(Cl)Cl.C(OCC)(=O)C>[Br:22][C:12]1[CH:13]=[C:8]([C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[CH3:1])[CH:9]=[N:10][C:11]=1[NH2:14]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 66278167HCID 66278167, compound

Product 1

HCID 118045721HCID 118045721, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To an ice cold solution of 3′-methyl-3,4′-bipyridin-6-amine (250 mg, 1.350 mmol) in DCM (4499 μL) was added NBS (264 mg, 1.485 mmol) in two portions. The reaction mixture was stirred at 0° C. for 2 h. Reaction mixture was diluted with ethyl acetate, and was washed with water, brine, dried and concentrated. Residue was treated heptane, the solid filtered to give 5-bromo-3′-methyl-3,4′-bipyridin-6-amine (350 mg, 1.325 mmol, 98% yield) as brown color solid, used in next step reaction without purification. LCMS (m/z): 264.4/266.4 (MH+), 0.32 min; 1H NMR (400 MHz, CDCl3) δ ppm 8.51 (s, 1H), 8.47 (d, J=5.1 Hz, 1H), 8.04 (d, J=2.0 Hz, 1H), 7.69 (d, J=2.0 Hz, 1H), 7.12 (d, J=5.1 Hz, 1H), 5.06 (br. s., 2H), 2.32 (s, 3H).

Workup

  1. customReaction mixture
  2. washwas washed with water, brine
  3. customdried
  4. concentrationconcentrated
  5. additionResidue was treated heptane
  6. filtrationthe solid filtered

Sources & evidence

ORD record
ord-4b0c3cfab0f7440cb4812827c552d763
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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