2,3-Difluorophenol → HCID 57919142, compound

HRID 2381333Notes

Reaction equation

HRID 2381333 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]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=1[OH:24].C[O:26][C:27](=[O:36])[CH:28](Br)[CH2:29][CH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>>[CH:30]1([CH2:29][CH:28]([N:4]2[C:3](=[O:15])[CH:2]=[C:7]([O:24][C:18]3[CH:19]=[CH:20][CH:21]=[C:22]([F:23])[C:17]=3[F:16])[CH:6]=[N:5]2)[C:27]([OH:26])=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

4

Reactant 3

HCID 808792,3-DifluorophenolHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919142HCID 57919142, compoundYield 63%

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 2,3-difluoro-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(2,3-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (14.91 g, 63%) as a white solid; ESI-MS 364 [M+H+]; HPLC: >95% (purity). 1H-NMR (300 MHz, CDCl3) δ 7.89-7.90 (d, 1H), 7.12-7.19 (m, 2H), 6.99-7.03 (m, 1H), 6.01 (s, 1H), 5.51-5.56 (m, 1H), 2.29-2.39 (m, 1H), 2.07-2.16 (m, 1H), 1.50-1.81 (m, 7H), 1.10-1.25 (m, 2H).

Sources & evidence

ORD record
ord-458a19069bc4407488059ed379933872
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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