3-Fluorophenol → HCID 57919130, compound

HRID 2381331Notes

Reaction equation

HRID 2381331 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[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1.C[O:25][C:26](=[O:35])[CH:27](Br)[CH2:28][CH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>>[CH:29]1([CH2:28][CH:27]([N:4]2[C:3](=[O:15])[CH:2]=[C:7]([O:23][C:19]3[CH:20]=[CH:21][CH:22]=[C:17]([F:16])[CH:18]=3)[CH:6]=[N:5]2)[C:26]([OH:25])=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

4

Reactant 3

HCID 97433-FluorophenolHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919130HCID 57919130, compoundYield 71%

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 3-fluoro-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(3-fluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (10.5 g, 71%); ESI-MS 347 [M+H+] HPLC: >96% (purity). 1H-NMR (300 MHz, CDCl3) δ 7.86 (s, 1H), 7.40-7.48 (m, 1H), 7.02-7.07 (t, 1H), 6.87-6.96 (m, 2H), 6.05 (s, 1H), 5.51-5.56 (m, 1H), 2.32-2.41 (m, 1H), 2.12-2.14 (m, 1H), 1.50-1.80 (m, 7H), 1.15-1.17 (m, 2H).

Sources & evidence

ORD record
ord-5aa353ff3f3744278758df4c40a29b34
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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