Triethylamine → HCID 49758339, compound

HRID 1626519Notes

Reaction equation

HRID 1626519 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[F:9][C:10]([F:21])([F:20])[C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.[F-].[Cs+].C(N(CC)CC)C>C(O)CC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[F:9][C:10]([F:21])([F:20])[C:11]1[CH:16]=[CH:15][C:14]([C:2]2[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 216436-Amino-3-chloropyridazineHCID 25953Cesium fluorideHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 49758339HCID 49758339, compoundYield 27.1%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 10311-PropanolSolvent

Procedure

To a solution of 6-chloropyridazin-3-amine (3.00 g, 23.2 mmol), 4-(trifluoromethyl)phenylboronic acid (5.72 g, 30.1 mmol), cesium fluoride (9.15 g, 60.2 mmol), triethylamine (4.84 mL, 34.7 mmol) in n-propanol (100 mL) degassed with argon was added dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.953 g, 1.16 mmol), and the reaction was heated to reflux for 3 hours. Water was added to precipitate solids, which were collected by filtrations. The solids were purified on a SP1 system (0-10% MeOH in EtOAc) to yield 6-(4-(trifluoromethyl)phenyl)pyridazin-3-amine (1.5 g, 6.27 mmol, 27.1% yield).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 3 hours
  3. customto precipitate solids, which
  4. filtrationwere collected by filtrations
  5. customThe solids were purified on a SP1 system (0-10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-19e961eb0094495da7211963d8c806a4
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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