2,6-Difluorophenol → HCID 57919339, compound

HRID 2381319Notes

Reaction equation

HRID 2381319 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]=[C:19]([F:23])[C:18]=1[OH:24].C[O:26][C:27](=[O:39])[CH:28](Br)[CH2:29][C:30]1[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:31]=1[F:37]>>[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=1[O:24][C:7]1[CH:6]=[N:5][N:4]([CH:28]([CH2:29][C:30]2[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:31]=2[F:37])[C:27]([OH:26])=[O:39])[C:3](=[O:15])[CH:2]=1

Participants

4

Reactant 3

HCID 943922,6-DifluorophenolHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919224HCID 57919224, compound2×

Product 1

HCID 57919339HCID 57919339, 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-phenol and alkylating with 2-bromo-3-(2,6-difluoro-phenyl)-propionic acid methyl ester (Intermediate 15) afforded 2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-(2,6-difluoro-phenyl)-propionic acid as a light yellow solid (1.35 g, 98% for the final step). 1H NMR (300 MHz, DMSO-d6) δ ppm 3.42 (d, J=7.6 Hz, 2H), 5.47 (t, J=7.6 Hz, 1H), 6.00 (d, J=2.7 Hz, 1H), 6.93-7.09 (m, 2H), 7.22-7.55 (m, 4H), 8.20 (d, J=2.7 Hz, 1H), 13.38 (br s, 1H).

Sources & evidence

ORD record
ord-30c01ca9908b4792ad849d8537cb2bd4
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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