N-bromobutanimide → Tert-butyl 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoate

HRID 596085Notes

Reaction equation

HRID 596085 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[NH2:9][C:10]1[C:15]([C:16]2[CH:28]=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[C:18]([F:29])[CH:17]=2)=[CH:14][CH:13]=[CH:12][N:11]=1>CC#N>[NH2:9][C:10]1[C:15]([C:16]2[CH:28]=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])=[C:18]([F:29])[CH:17]=2)=[CH:14][C:13]([Br:8])=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118045884Tert-butyl 4-(2-aminopyridin-3-yl)-2-fluorobenzoate

Product 1

HCID 118046192Tert-butyl 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

NBS (2.145 g, 12.05 mmol) was added to a room temperature solution of tert-butyl 4-(2-aminopyridin-3-yl)-2-fluorobenzoate (3.31 g, 11.48 mmol) in MeCN (60 mL). The resulting mixture was stirred for 10 min. The reaction was quenched with 1:1 of sat. aq. Na2S2O3:sat. aq. NaHCO3 solution, and then extracted into ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo yielding tert-butyl 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoate. The material was used without further purification. LCMS (m/z): 369.0 (MH+), 0.85 min.

Workup

  1. customThe reaction was quenched with 1:1 of sat. aq. Na2S2O3
  2. extractionaq. NaHCO3 solution, and then extracted into ethyl acetate
  3. washThe combined organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-713e754a60df4fefa90af660001323b0
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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