5-bromo-2-(4-fluorophenyl)-4-methoxy-3(2H)-pyridazinone → 2-(4-Fluorophenyl)-4-methoxy-5-[4-(methylthio)phenyl]-3(2H)-pyridazinone

HRID 891321Notes

Reaction equation

HRID 891321 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]([O:15][CH3:16])=[C:11](Br)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH3:18][S:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]([O:15][CH3:16])=[C:11]([C:23]3[CH:24]=[CH:25][C:20]([S:19][CH3:18])=[CH:21][CH:22]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 14874955-bromo-2-(4-fluorophenyl)-4-methoxy-3(2H)-pyridazinoneHCID 27339594-(Methylthio)phenylboronic acid

Product 1

HCID 219341922-(4-Fluorophenyl)-4-methoxy-5-[4-(methylthio)phenyl]-3(2H)-pyridazinone

Procedure

The title compound was prepared according to the method of Example 6 starting with 2-(4-fluorophenyl)-4-methoxy-5-bromo-3(2H)-pyridazinone in place of 2-benzyl-4-bromo-5-methoxy-3(2H)-pyridazinone and substituting 4-(methylthio)benzeneboronic acid in place of 4-fluorobenzeneboronic acid (yield: 70 mg, 61%). 1H NMR (500 MHz, DMSO-d6) δ 2.54 (s, 3H), 4.02 (s, 3H), 7.35 (dd, J=9.0, 9.0 Hz, 2H), 7.39 (d, J=8.5 Hz, 2H), 7.61 (d, J=8.5 Hz, 2H), 7.65 (dd, J=9.0, 5.0 Hz, 2H), 8.14 (s, 1H). MS (APCI+) m/z 343 (M+H)+.

Sources & evidence

ORD record
ord-b729fc2f64994fc089fa79ebb0ae6275
Source dataset
uspto-grants-2006_02
Patent number
US07001895B2

Reaction notes

Loading…