2,6-Difluorophenol → HCID 57919097, compound

HRID 2381313Notes

Reaction equation

HRID 2381313 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:34])[CH:28](Br)[CH2:29][CH:30]([CH3:32])[CH3:31]>>[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]([CH3:32])[CH3:31])[C:27]([OH:26])=[O:34])[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 12957039Methyl 2-bromo-4-methylpentanoate2×

Product 1

HCID 57919097HCID 57919097, 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-methyl-pentanoic acid methyl ester (Intermediate 11) afforded 2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-4-methyl-pentanoic acid as a white solid (1.48 g, 89% for the final step); ES+-HRMS m/e calcd for C16H16N2O4F2 [M+H+] 361.0970, found 361.0969. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.86 (d, J=6.0 Hz, 6H), 1.24-1.45 (m, 1H), 1.84 (ddd, J=14.0, 9.5, 4.3 Hz, 1H), 2.04-2.18 (m, 1H), 5.39 (dd, J=11.1, 4.3 Hz, 1H), 6.08 (d, J=2.7 Hz, 1H), 7.30-7.44 (m, 2H), 7.44-7.57 (m, 1H), 8.28 (d, J=2.7 Hz, 1H), 13.09 (br s, 1H).

Sources & evidence

ORD record
ord-5c9556161a1746eaa5dae8f997c1aaca
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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