N-bromobutanimide → HCID 118045604, compound

HRID 595823Notes

Reaction equation

HRID 595823 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][S:10](=[O:14])(=[O:13])[CH2:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Br:22])C(=O)C1>C(#N)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][S:10](=[O:14])(=[O:13])[CH2:9]2)=[CH:4][C:3]=1[Br:22]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118046480HCID 118046480, compound

Product 1

HCID 118045604HCID 118045604, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

3-(6-aminopyridin-3-yl)tetrahydrothiophene 1,1-dioxide (96 mg, 0.452 mmol) was dissolved in acetonitrile (5 mL) and the solution was cooled to 0° C., to it was added NBS (80 mg, 0.452 mmol) and the mixture was stirred at 0° C. for 40 min. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between EtOAc/sat. NaHCO3 (30 mL/20 mL), the EtOAc layer was washed with sat. Na2CO3 (20 mL), brine (20 mL), dried (Na2SO4), filtered off and concentrated in vacuo yielding 3-(6-amino-5-bromopyridin-3-yl)tetrahydrothiophene 1,1-dioxide as light brown oil (50 mg, 38% yield). LCMS (m/z): 293.0/291.0 (MH+), 0.29 min.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between EtOAc/
  3. washNaHCO3 (30 mL/20 mL), the EtOAc layer was washed with sat. Na2CO3 (20 mL), brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered off
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ce5a4f43e79c4f9db6ba01a310b1af33
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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