2,6-Difluorophenol → HCID 57919231, compound

HRID 2381316Notes

Reaction equation

HRID 2381316 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:36])[CH:28](Br)[CH2:29][CH:30]([CH2:33][CH3:34])[CH2:31][CH3:32]>>[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][CH:30]([CH2:33][CH3:34])[CH2:31][CH3:32])[C:27]([OH:26])=[O:36])[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 57919166HCID 57919166, compound2×

Product 1

HCID 57919231HCID 57919231, 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-4-ethyl-hexanoic acid methyl ester (Intermediate 17) afforded 2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-4-ethyl-hexanoic acid as a white solid (599.8 mg, 88% for the final step); ES+-HRMS m/e calcd for C18H20N2O4F2 [M+H+] 367.1464, found 367.1462. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.77 (m, 6H), 1.00 (br s, 1H), 1.09-1.44 (m, 4H), 1.93 (ddd, J=14.2, 9.4, 4.3 Hz, 1H), 2.11 (ddd, J=14.2, 10.8, 4.0 Hz, 1H), 5.38 (dd, J=10.8, 4.0 Hz, 1H), 6.09 (d, J=2.7 Hz, 1H), 7.32-7.43 (m, 2H), 7.43-7.57 (m, 1H), 8.28 (d, J=2.7 Hz, 1H), 13.11 (br s, 1H).

Sources & evidence

ORD record
ord-e3c3d664b15b471d89008a2de321f8d3
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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