N-bromobutanimide → 4-(4-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)-2-chlorobenzonitrile

HRID 872869Notes

Reaction equation

HRID 872869 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[N:14]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][O:16]3)[N:13]=[CH:12][CH:11]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Br:21]N1C(=O)CCC1=O.OS([O-])=O.[Na+]>C(#N)C>[Br:21][C:11]1[CH:12]=[N:13][N:14]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[C:10]=1[C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Cl:1])[CH:9]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 23665763Sodium BisulfiteHCID 706562532-chloro-4-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)benzonitrile

Product 1

HCID 706557724-(4-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)-2-chlorobenzonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-chloro-4-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)benzonitrile (10 g, 34.8 mmol) and acetonitrile (120 ml) were added into a flask and the temperature was adjusted to 0° C. with an ice bath. N-bromosuccinimide (6.80 g, 38.2 mmol) was added in small batches keeping the temperature below 5° C. The mixture was stirred at room temperature for 3 h. 10% NaHSO3 (100 ml) was added and the mixture was stirred for 15 min. The reaction mixture was extracted with DCM. The combined organic phases were dried, filtered and evaporated. The product was purified by recrystallization from ethanol. Yield 82%. 1H-NMR (400 MHz; DMSO-d6): δ 1.51-1.59 (m, 2H), 1.62-1.76 (m, 1H), 1.90-2.00 (m, 2H), 2.06-2.18 (m, 1H), 3.62-3.70 (m, 1H), 3.91-3.98 (m, 1H), 5.49 (dd, 1H), 8.02 (dd, 1H), 8.09 (d, 1H), 8.12 (d, 1H), 8.38 (s, 1H).

Workup

  1. customthe temperature was adjusted to 0° C. with an ice bath
  2. customthe temperature below 5° C
  3. stirringthe mixture was stirred for 15 min
  4. extractionThe reaction mixture was extracted with DCM
  5. customThe combined organic phases were dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe product was purified by recrystallization from ethanol

Sources & evidence

ORD record
ord-5642cd15938c4f3b9b6c430da8d10167
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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