Bromine → HCID 86611752, compound

HRID 2239876Notes

Reaction equation

HRID 2239876 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][C:3]=1[CH2:9][CH3:10].ClC1C(CC)=C(N)N=NC=1.C([O-])(O)=O.[Na+].[Br:26]Br>CO.CCOC(C)=O>[Br:26][C:4]1[C:3]([CH2:9][CH3:10])=[C:2]([Cl:1])[N:7]=[N:6][C:5]=1[NH2:8]

Participants

7

Reactant 4

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 18995742HCID 18995742, compoundHCID 68484213HCID 68484213, compound

Product 1

HCID 86611752HCID 86611752, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 6-Chloro-5-ethylpyridazin-3-amine and chloro-4-ethylpyridazin-3-amine (3.50 g, 0.022 mol) from 1b and NaHCO3 (3.73 g, 0.044 mol, 2 eq) were suspended in MeOH (20 mL) and treated with Br2 (1.25 mL, 0.024 mol). The mixture was stirred at room temperature for 24 h, then filtered. The filtrate was condensed in vacuo. The resulting residue was resuspended in EtOAc (100 mL) and washed sequentially with sat. aqueous NaHCO3 solution (2×20 mL) and aqueous NaCl solution (1×20 mL). The solution was dried over sodium sulfate. The solvent was removed in vacuo to give crude 4-bromo-6-chloro-5-ethylpyridazin-3-amine. LC/MS, m/e 236 (M+1). HPLC Rt, 2.15 min. Waters Sunfire C18 column (4.6×50 mm). 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B=0, final % B=100, gradient time 4 min, hold at 100% B 1 min, flow rate 4 mL/min.

Workup

  1. filtrationfiltered
  2. customcondensed in vacuo
  3. washwashed sequentially with sat. aqueous NaHCO3 solution (2×20 mL) and aqueous NaCl solution (1×20 mL)
  4. dry with materialThe solution was dried over sodium sulfate
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d7b0a3bceeb14f3d9303fefc12ecdaa4
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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