N-bromobutanimide → HCID 118045194, compound

HRID 595814Notes

Reaction equation

HRID 595814 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][S:11](=[O:15])(=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Br:23])C(=O)C1>C(Cl)Cl.C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][S:11](=[O:15])(=[O:14])[CH2:12][CH2:13]2)=[CH:4][C:3]=1[Br:23]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 118045401HCID 118045401, compound

Product 1

HCID 118045194HCID 118045194, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To an ice cold solution of 4-(6-aminopyridin-3-yl)tetrahydro-2H-thiopyran 1,1-dioxide (140 mg, 0.62 mmol) in DCM (15 mL) was added NBS (110 mg, 0.62 mmol) in two portions. The reaction mixture was stirred at 0° C. for 20 min. The reaction solution was diluted with ethyl acetate, washed with water, saturated aqueous sodium bicarbonate solution, brine, dried over sodium sulfate and concentrated to give 4-(6-amino-5-bromopyridin-3-yl)tetrahydro-2H-thiopyran 1,1-dioxide (190 mg, 0.62 mmol). LCMS (m/z): 305/307 (MH+), 0.33 min.

Workup

  1. washwashed with water, saturated aqueous sodium bicarbonate solution, brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-228e7fb991c0406289f248fcb5bfe9be
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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