Potassium Carbonate → 6-Chloro-N-(2-(4-fluorophenyl)-2-methylpropyl)pyridazin-3-amine

HRID 869134Notes

Reaction equation

HRID 869134 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[CH2:9][NH2:10])=[CH:4][CH:3]=1.[Cl:13][C:14]1[N:15]=[N:16][C:17](Cl)=[CH:18][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>C(O)(C)C>[Cl:13][C:14]1[N:15]=[N:16][C:17]([NH:10][CH2:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)([CH3:12])[CH3:11])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 673313,6-DichloropyridazineHCID 212510232-(4-Fluorophenyl)-2-methylpropan-1-amine

Product 1

HCID 866861256-Chloro-N-(2-(4-fluorophenyl)-2-methylpropyl)pyridazin-3-amineYield 105.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of (2-(4-fluorophenyl)-2-methylpropan-1-amine (27 g, 160 mmol, 1.6 equiv), 3,6-dichloropyridazine (15 g, 100 mmol, 1.0 equiv) and K2CO3 (42 g, 302 mmol, 3.0 equiv) in isopropanol (15 mL) was stirred at 100° C. for 36 hours. The cooled mixture was partitioned between water and EtOAc and the organic fraction was dried over Na2SO4 and concentrated in vacuo. Partial purification over silica gel using a 30-75% gradient of EtOAc/hexanes gave the desired product (29.6 g, 103%) which was used without further purification.

Workup

  1. customThe cooled mixture was partitioned between water and EtOAc
  2. dry with materialthe organic fraction was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customPartial purification over silica gel using a 30-75% gradient of EtOAc/hexanes

Sources & evidence

ORD record
ord-557e40dceda546f4afe31eb2027404e1
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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