Bromine → HCID 15896326, compound

HRID 566714Notes

Reaction equation

HRID 566714 reaction equation
BrBr.[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[CH2:12][C:13](=[O:16])[NH:14][N:15]=2)=[CH:6][CH:5]=1>C(O)(=O)C>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([C:17]3[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=3)=[CH:12][C:13](=[O:16])[NH:14][N:15]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 15896325HCID 15896325, compound

Product 1

HCID 15896326HCID 15896326, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

A solution of bromine (78.3 μl, 1.48 mmol) in acetic acid (6 ml) was added dropwise to a stirred solution of 6-(4-fluorophenyl)-4,5-dihydro-5-(4-pyridyl)-2H-pyridazin-3-one (314 mg, 1.17 mmol) in acetic acid (4.6 ml) at room temperature. After 2 h at room temperature, more bromine (41.7 μl, 0.78 mmol) in acetic acid (3.2 ml) was added to the turbid mixture. A gum precipitated. After 30 minutes, it was evaporated and co-evaporated with toluene. Residual acid was neutralized with methanolic 2N ammonia followed by evaporation. The resulting product was purified on a column of silica gel (3-5% methanol/dichloromethane) to provide the title compound as a solid. MS (m/z): 268.1 (M+H)+; C15H16FN3O requir. 267.3.

Workup

  1. customA gum precipitated
  2. waitAfter 30 minutes
  3. customit was evaporated
  4. customfollowed by evaporation
  5. customThe resulting product was purified on a column of silica gel (3-5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-7e7bbc0072424cb4ae7fa47081f7f1ec
Source dataset
uspto-grants-2001_01
Patent number
US06174901B1

Reaction notes

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