N-bromobutanimide → Methyl 4-(2-amino-5-bromopyridin-3-yl)-2-methylbenzoate

HRID 596081Notes

Reaction equation

HRID 596081 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([CH3:18])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C1C(=O)N([Br:26])C(=O)C1>C(#N)C>[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([CH3:18])[CH:9]=2)=[CH:6][C:5]([Br:26])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118046459Methyl 4-(2-aminopyridin-3-yl)-2-methylbenzoate

Product 1

HCID 118045889Methyl 4-(2-amino-5-bromopyridin-3-yl)-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 4-(2-aminopyridin-3-yl)-2-methylbenzoate (4.2 g, 17.34 mmol) in acetonitrile (173 mL) was added NBS (3.15 g, 17.68 mmol) in two portions at 0° C. The reaction mixture was stirred at 0° C. for 20 min. LCMS showed the reaction completed. After quenched with sat. Na2SO3 and NaHCO3, the reaction mixture was stirred for 30 min. The reaction mixture was extracted with EtOAc 3 times, washed by sat NaHCO3, water and brine. The organics was dried over Na2SO4, filtered and concentrated. The crude material was triturated with ether and taken to the next step without further purification. LCMS (m/z): 323.1 (MH+), 0.68 min.

Workup

  1. customAfter quenched with sat. Na2SO3 and NaHCO3
  2. stirringthe reaction mixture was stirred for 30 min
  3. extractionThe reaction mixture was extracted with EtOAc 3 times
  4. washwashed
  5. dry with materialThe organics was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was triturated with ether
  9. customtaken to the next step without further purification
  10. custom323.1 (MH+), 0.68 min.

Sources & evidence

ORD record
ord-4829d1540229494ab22631d82ec9770f
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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