Bromine → HCID 22037579, compound

HRID 861044Notes

Reaction equation

HRID 861044 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[CH:11][N:10]([CH3:19])[N:9]=2)=[CH:4][CH:3]=1.[Br:20]Br>C(O)(=O)C.CN(C=O)C>[Br:20][C:11]1[N:10]([CH3:19])[N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:12]=1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 22037373HCID 22037373, compound

Product 1

HCID 22037579HCID 22037579, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-[3-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]pyridine (2.7 g, 10.67 mmol) (prepared in accordance with Example A-212) in acetic acid (30 mL) and DMF (13 mL) was added bromine (19.5 g, 122.0 mmol). The solution was heated at 80° C. overnight. TLC indicated that the reaction was complete. The mixture was quenched slowly with K2CO3 (25 g). When pH was about 5, a precipitate was formed. The precipitate was washed with water (50 mL×5) to give 4-[5-bromo-3-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]pyridine (1.24 g, 35%): mp 174.38° C.; Mass spectrum m/z=332, 334; 1H NMR was consistent with the proposed structure. Anal. Calc'd for C15H11N3FBr.0.2H2O: C, 53.66; H, 3.42; N, 12.51. Found: C, 53.58; H, 3.12; N, 12.43.

Workup

  1. customThe mixture was quenched slowly with K2CO3 (25 g)
  2. customWhen pH was about 5, a precipitate was formed
  3. washThe precipitate was washed with water (50 mL×5)

Sources & evidence

ORD record
ord-335d3a1032ec43b1a873cf516df13a5e
Source dataset
uspto-grants-2006_12
Patent number
US07153959B2

Reaction notes

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