N-bromobutanimide → Methyl 2-amino-5-bromoisonicotinate

HRID 420519Notes

Reaction equation

HRID 420519 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH2:10])[CH:5]=1.C1C(=O)N([Br:19])C(=O)C1>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[C:9]([Br:19])=[CH:8][N:7]=[C:6]([NH2:10])[CH:5]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 236984Methyl 2-aminopyridine-4-carboxylate

Product 1

HCID 25307230Methyl 2-amino-5-bromoisonicotinateYield 35.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-18 °C

Procedure

A solution of 2-amino-isonicotinic acid methyl ester (5.58 g, 36.7 mmol) in DMF (56 mL) was cooled to −18° C. (ice/MeOH bath), treated with NBS (7.21 g, 38.5 mmol), and stirred at −18° C. for 1 h. The reaction mixture was diluted in AcOEt (500 mL) and washed with water (2×250 mL). The organic layer was dried over Na2SO4, filtered and evaporated to yield the crude title compound (3.0 g, 13.0 mmol, 35%) as a yellow solid, which was used in the next step without further purification. MS: 231 [M+1]+; HPLC: AtRet=0.70.

Workup

  1. washwashed with water (2×250 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-e9ee3d3716b4441ea531b3b4e400860c
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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