N-bromobutanimide → HCID 86670211, compound

HRID 2091580Notes

Reaction equation

HRID 2091580 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3([C:20]#[N:21])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[Br:22]N1C(=O)CCC1=O>CN(C=O)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]3([C:20]#[N:21])[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[CH:12][CH:13]=2)=[N:6][C:7]=1[Br:22]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 70654899HCID 70654899, compound

Product 1

HCID 86670211HCID 86670211, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-(5-aminopyrazin-2-yl)phenyl)tetrahydro-2H-pyran-4-carbonitrile (1.08 m, 3.84 mmol) in DMF (30 mL) was added N-bromosuccinimide (747 mg, 4.22 mmol) in one portion. The reaction was then stirred at room temperature for 1 h. At completion, the mixture was poured over ice (50 mL) and stirred for 20 min. After filtration and washing with water and drying under vacuum, 4-(4-(5-amino-6-bromopyrazin-2-yl)phenyl)tetrahydro-2H-pyran-4-carbonitrile was obtained as obtained as a dark brown solid (1.37 g, 100% yield).

Workup

  1. stirringstirred for 20 min
  2. filtrationAfter filtration
  3. washwashing with water
  4. customdrying under vacuum

Sources & evidence

ORD record
ord-2cbb2a6878fe4dc0940fbe8370120b89
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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