2-Methoxybenzoyl chloride → HCID 25212305, compound

HRID 572330Notes

Reaction equation

[CH3:1][C:2]1[C:3]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[N:4][O:5][C:6]=1[C:7]([F:10])([F:9])[F:8].[CH3:16][O:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>>[CH3:16][O:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([C:13]1[S:12][C:11]([C:3]2[C:2]([CH3:1])=[C:6]([C:7]([F:8])([F:10])[F:9])[O:5][N:4]=2)=[CH:15][CH:14]=1)=[O:21]

Participants

Reactant 2

HCID 889692-Methoxybenzoyl chloride

HCID 57606117HCID 57606117, compound

Product 1

HCID 25212305HCID 25212305, compoundYield 54%

Procedure

Prepared from 4-Methyl-3-thiophen-2-yl-5-trifluoromethyl-isoxazole and 2-methoxybenzoyl chloride by the method described in Example 3. Crude product was chromatographed on silica gel with EtOAc/hexanes (15 then 25%) as eluant to afford product as a yellow-tinted oil (100 mg, 54%). 1H NMR (CDCl3) 2.39 (d, J=1.3, 3H), 3.82 (s, 3H), 7.01-7.08 (m, 2H), 7.27-7.54 (m, 4H). 13C NMR 8.0, 55.9, 111.9, 115.9 (q, J=151), 120.7, 128.2, 129.0, 129.6, 132.7, 135.0, 136.3, 147.1, 155.4 (q, J=41), 157.3, 158.0, 188.2. 19F NMR −63.1. LC/MS 7.50 min, [M+1]+ 368.

Workup

customCrude product was chromatographed on silica gel with EtOAc/hexanes (15

Sources & evidence

ORD record: ord-6f3cfc5eed5042d896a943d479f46424
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029397B2

Reaction notes

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