1,1,1-Trifluoro-2-iodoethane → 2-(2,2,2-Trifluoroethyl)4-(4-chlorophenyl)-5-[4-(methylsulfinyl)phenyl]-3(2H)-pyridazinone

HRID 891293Notes

Reaction equation

HRID 891293 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.I[CH2:12][C:13]([F:16])([F:15])[F:14].C([N:24]1[C:29](=[O:30])[C:28](Cl)=[C:27]([C:32]2[CH:37]=[CH:36][C:35]([S:38][CH3:39])=[CH:34][CH:33]=2)[CH:26]=[N:25]1)C1C=CC=CC=1.ClC1C=C(C=CC=1)C(OO)=[O:45]>>[F:14][C:13]([F:16])([F:15])[CH2:12][N:24]1[C:29](=[O:30])[C:28]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[C:27]([C:32]2[CH:37]=[CH:36][C:35]([S:38]([CH3:39])=[O:45])=[CH:34][CH:33]=2)[CH:26]=[N:25]1

Participants

5

Reactant 4

HCID 677091,1,1-Trifluoro-2-iodoethaneHCID 70297m-Chloroperbenzoic acidHCID 742994-Chlorophenylboronic acidHCID 219339762-benzyl-4-chloro-5-[4-(methylthio)phenyl]-3(2H)-pyridazinone

Product 1

HCID 103424332-(2,2,2-Trifluoroethyl)4-(4-chlorophenyl)-5-[4-(methylsulfinyl)phenyl]-3(2H)-pyridazinoneYield 70%

Procedure

2-Benzyl-4-chloro-5-methoxy-3(2H)-pyridazinone (J. Het. Chem., 1996, 33, 1579-1582) was converted to the 5-hydroxy-analog according to the method of Example 7 and then to the 5-trifluoromethylsulfonyloxy-analog according to the method of Example 8. Subsequent coupling to 4-(methylthio)phenylboronic acid, according to the method of Example 9, provided 2-benzyl-4-chloro-5-[4-(methylthio)phenyl]-3(2H)-pyridazinone. This intermediate was coupled with 4-chlorophenylboronic acid according to the method of Example 6. This product was N-debenzylated according to the method of Example 11 and N-alkylated with 2-iodo-1,1,1-trifluoroethane according to the method of Example 20. The resulting sulfide was oxidized to the corresponding sulfoxide with one equivalent of meta-chloroperoxybenzoic acid, according to the method of Example 5 to provide the title compound (yield: 130 mg, 70%). mp 154-155° C. 1H NMR (300 MHz, CDCl3) δ 2.74 (s, 3H), 4.88 (q, J=9 Hz, 2H), 7.14 (d, J=9 Hz, 2H), 7.26 (d, J=9 Hz, 2H), 7.31 (d, J=9 Hz, 2H), 7.61 (d, J=9 Hz, 2H), 7.82 (s, 1H). MS (DCI/NH3) m/z 427 (M+H)+. Anal. calc. for C19H14ClF3N2O2S: C, 53.46; H, 3.3; N, 6.56. Found: C, 53.58; H, 3.34; N, 6.42.

Sources & evidence

ORD record
ord-ae029ab9413f4faa93e6a9e01bf41c7c
Source dataset
uspto-grants-2006_02
Patent number
US07001895B2

Reaction notes

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