2-(4-fluorophenyl)-4-methoxy-5-[4-(methylseleno)phenyl]-3(2H)-pyridazinone → 2,4-Bis(4-fluorophenyl)-5-[4-(methylseleno)phenyl]-3(2H)-pyridazinone

HRID 381980Notes

Reaction equation

HRID 381980 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12](OC)=[C:11]([C:17]3[CH:22]=[CH:21][C:20]([Se:23][CH3:24])=[CH:19][CH:18]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.C[Se]C1C=CC(B(O)O)=CC=1.[F:36][C:37]1[CH:42]=[CH:41][C:40](N2C(=O)C(OC)=C(C3C=CC(SC)=CC=3)C=N2)=[CH:39][CH:38]=1.FC1C=CC([Mg]Br)=CC=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]([C:40]3[CH:41]=[CH:42][C:37]([F:36])=[CH:38][CH:39]=3)=[C:11]([C:17]3[CH:22]=[CH:21][C:20]([Se:23][CH3:24])=[CH:19][CH:18]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 219341592-(4-fluorophenyl)-4-methoxy-5-[4-(methylseleno)phenyl]-3(2H)-pyridazinoneHCID 219341922-(4-Fluorophenyl)-4-methoxy-5-[4-(methylthio)phenyl]-3(2H)-pyridazinoneHCID 21934282(4-(Methylselanyl)phenyl)boronic acidHCID 178418676HCID 178418676, compound

Product 1

HCID 101389552,4-Bis(4-fluorophenyl)-5-[4-(methylseleno)phenyl]-3(2H)-pyridazinone

Procedure

The title compound was prepared according to the method of Example 228, substituting 2-(4-fluorophenyl)-4-methoxy-5-[4-(methylseleno)phenyl]-3(2H)-pyridazinone (prepared according to the method of Example 194C, substituting 4-(methylseleno)benzeneboronic acid from Example 1 in place of 4-(methylthio)benzeneboronic acid) in place of 2-(4-fluorophenyl)-4-methoxy-5-[4-(methylthio)phenyl]-3-(2H)-pyridazinone and substituting 4-fluorophenyl magnesium bromide in place of cyclohexylmagnesium chloride (yield: 44 mg, 69%). 1H NMR (300 MHz, CDCl3) δ 2.37 (s, 3H), 6.98 (dd, J=8.8, 8.8 Hz, 2H), 7.05 (d, J=8.7 Hz, 2H), 7.17 (dd, J=8.7, 8.7 Hz, 2H), 7.23-7.31 (m, 2H), 7.32 (d, J=8.7 Hz, 2H), 7.65-7.72 (m, 2H), 8.00 (s, 1H). MS (APCI+) m/z 455 (M+H)+.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-23ab63751d8a4900a6981ac5eb534070
Source dataset
uspto-grants-2001_10
Patent number
US06307047B1

Reaction notes

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