2-Fluorophenol → HCID 57919288, compound

HRID 2381332Notes

Reaction equation

HRID 2381332 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:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23].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:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[F:16])[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 97072-FluorophenolHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919288HCID 57919288, compoundYield 70%

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-fluoro-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(2-fluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (10.2 g, 70%); ESI-MS 347 [M+H+]; HPLC: >98% (purity). 1H-NMR (300 MHz, CDCl3) δ 7.91 (s, 1H), 7.18-7.33 (m, 4H), 5.98 (s, 1H), 5.51-5.56 (m, 1H), 2.30-2.40 (m, 1H), 2.07-2.16 (m, 1H), 1.50-1.80 (m, 7H), 1.11-1.21 (m, 2H).

Sources & evidence

ORD record
ord-d7b383ded6b54429a22688e46d121199
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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