N-bromobutanimide → HCID 86700378, compound

HRID 879555Notes

Reaction equation

HRID 879555 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[N:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=3)=[CH:8][CH:9]=2)[CH:4]=[N:3]1.C1C(=O)N([Br:25])C(=O)C1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:25][C:15]1[C:14]([NH2:17])=[CH:13][CH:12]=[C:11]([C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:2]([CH3:1])[N:3]=[CH:4]3)[N:16]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 86700377HCID 86700377, compound

Product 1

HCID 86700378HCID 86700378, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

In a 50 mL round bottom flask, 6-(1-methyl-1H-indazol-5-yl)pyridin-3-amine (225 mg, 1.00 mmol) was dissolved in DMF (8 mL) at room temperature and the solution was cooled down to 0° C. for 5 min under argon atmosphere. A solution of NBS (179 mg, 1.00 mmol) in DMF (6 mL) was added dropwise. The resulting reaction mixture was stirred at 0° C. for 30 min and then was poured onto saturated aq NaHCO3 solution (30 mL). EtOAc (3×30 mL) was used for extraction. Organic phase was then washed with water (2×20 mL) and concentrated. Residue was purified on silica gel column with 0-30% to afford product. LCMS-ESI+: calc'd for: C13H11BrN4: 303.0, 305.0 (M+H+); found: 303.1, 305.1 (M+H+)

Workup

  1. customThe resulting reaction mixture
  2. extractionEtOAc (3×30 mL) was used for extraction
  3. washOrganic phase was then washed with water (2×20 mL)
  4. concentrationconcentrated
  5. customResidue was purified on silica gel column with 0-30%
  6. customto afford product

Sources & evidence

ORD record
ord-7485eebdbb7d4364b8c9dc3e1a9d50bf
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

Loading…