Potassium Carbonate → 2-(3,4-Difluorophenyl)-4-(3-hydroxy-3-methylbutoxy)-5-[4-(methylsulfanyl)phenyl]pyridazin-3(2H)-one

HRID 891411Notes

Reaction equation

HRID 891411 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:14](=[O:15])[C:13]([O:16][CH2:17][CH2:18][C:19]([OH:22])([CH3:21])[CH3:20])=[C:12](Br)[CH:11]=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:24][S:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>C(O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:14](=[O:15])[C:13]([O:16][CH2:17][CH2:18][C:19]([OH:22])([CH3:21])[CH3:20])=[C:12]([C:29]3[CH:30]=[CH:31][C:26]([S:25][CH3:24])=[CH:27][CH:28]=3)[CH:11]=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27339594-(Methylthio)phenylboronic acidHCID 219342275-Bromo-2-(3,4-difluorophenyl)-4-(3-hydroxy-3-methylbutoxy)pyridazin-3(2H)-one

Product 1

HCID 219343582-(3,4-Difluorophenyl)-4-(3-hydroxy-3-methylbutoxy)-5-[4-(methylsulfanyl)phenyl]pyridazin-3(2H)-oneYield 64.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolvent

Procedure

The product from Example 471C (12.79 g, 32.86 mmol) was coupled to 4-(methyl-thio)phenylboronic acid (6.07 g, 36.15 mmol) with K2CO3 (10 g, 72.3 mmol) and PdCl2(PPh3)2 (1.15 g, 1.64 mmol) in ethanol (200 mL) at 60-65° C. for 40-70 minutes to provide the title intermediate (yield: 9.16 g, 64.5%).

Sources & evidence

ORD record
ord-bba9fb655a81447ba8d80c734089d95d
Source dataset
uspto-grants-2006_02
Patent number
US07001895B2

Reaction notes

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