Triethylamine → HCID 59369950, compound

HRID 1924761Notes

Reaction equation

HRID 1924761 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[CH:13]=[CH:12][C:11](=[O:14])[C:10]([C:15]3[N:16]([C:20]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH:23]=[CH:22][CH:21]=4)[N:17]=[CH:18][CH:19]=3)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[F:30][CH2:31][CH2:32][OH:33].CCN(CC)CC.[C]=O.C[CH2:44][O:45]C(C)=O>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]>[F:30][CH2:31][CH2:32][O:33][C:44](=[O:45])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH:13]=[CH:12][C:11](=[O:14])[C:10]([C:15]3[N:16]([C:20]4[C:21]5[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=5)[CH:27]=[CH:28][CH:29]=4)[N:17]=[CH:18][CH:19]=3)=[N:9]2)[CH:3]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 97372-FluoroethanolHCID 593700971-(3-Bromo-phenyl)-3-(2-naphthalen-1-yl-2H-pyrazol-3-yl)-1H-pyridazin-4-oneHCID 178418416HCID 178418416, compound

Product 1

HCID 59369950HCID 59369950, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

1-(3-Bromo-phenyl)-3-(2-naphthalen-1-yl-2H-pyrazol-3-yl)-1H-pyridazin-4-one (example 190) (100 mg, 0.23 mmol) was dissolved in EtOAc (3 ml) and the solution was placed in the reaction vessel. [PdCl2(dppf)] (10 mg) was added followed by 2-fluoroethanol (97 mg, 1.5 mmol) and Et3N (0.05 ml). The reactor was closed and the mixture was stirred 20 h under 70 bar carbon monoxide at 110° C. After evaporation of the solvents the residue was purified by chromatography (10 g SiO2, Hept to Hept/EtOAc 1:1). The product was isolated as an off-white solid (69 mg, 67%). MS: M=455.1 (M+H)+

Workup

  1. customThe reactor was closed
  2. customAfter evaporation of the solvents the residue
  3. customwas purified by chromatography (10 g SiO2, Hept to Hept/EtOAc 1:1)

Sources & evidence

ORD record
ord-33bc4a9aa7574fcc919a5367e76de3da
Source dataset
uspto-grants-2012_05
Patent number
US08178538B2

Reaction notes

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