2,6-Difluoro-3-methylphenol → HCID 57919338, compound

HRID 2381393Notes

Reaction equation

HRID 2381393 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[F:16][C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[C:19]([F:24])[C:18]=1[OH:25].C[O:27][C:28](=[O:37])[CH:29](Br)[CH2:30][CH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1>>[CH:31]1([CH2:30][CH:29]([N:4]2[C:3](=[O:15])[CH:2]=[C:7]([O:25][C:18]3[C:19]([F:24])=[CH:20][CH:21]=[C:22]([CH3:23])[C:17]=3[F:16])[CH:6]=[N:5]2)[C:28]([OH:27])=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

4

Reactant 3

HCID 27741522,6-Difluoro-3-methylphenolHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919338HCID 57919338, compound

Procedure

In an analogous manner to the stepwise sequence outlined in Intermediate 19, starting from 4,5-dichloro-2-(tetrahydropyran-2-yl)-2H-pyridazin-3-one (Intermediate 20) and 2,6-difluoro-3-methyl-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded impure 3-cyclopentyl-2-[4-(2,6-difluoro-3-methyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid as an oily light brown semi-solid (716.0 mg, 87% for the final step) and was used in Example 107.

Sources & evidence

ORD record
ord-d842085d2fb7462f84074ee2e947e705
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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