4-Cyanobenzoyl chloride → HCID 25211605, compound

HRID 572300Notes

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].[C:16]([C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1)#[N:17]>>[CH3:1][C:2]1[C:3]([C:11]2[S:12][C:13]([C:22]([C:21]3[CH:25]=[CH:26][C:18]([C:16]#[N:17])=[CH:19][CH:20]=3)=[O:23])=[CH:14][CH:15]=2)=[N:4][O:5][C:6]=1[C:7]([F:8])([F:10])[F:9]

Participants

Reactant 2

HCID 801724-Cyanobenzoyl chloride

HCID 57606117HCID 57606117, compound

Product 1

HCID 25211605HCID 25211605, compoundYield 36%

Procedure

Prepared from 4-Methyl-3-thiophen-2-yl-5-trifluoromethyl-isoxazole and 4-cyanobenzoyl chloride by the method described in Example 3. Crude product was chromatographed on silica gel with EtOAc/hexanes (10 then 20%) as eluant to afford product as a colorless solid (130 mg, 36%). 1H NMR (CDCl3) 2.42 (d, J=1.3, 3H), 7.62 (d, J=4.0, 1 H), 7.67 (d, J=4.0, 1H), 7.85 (d, J=8.3, 1H), 7.98 (d, J=7.9, 1H). 13C NMR 8.0, 114.9, 116.3, 118.7 (q, J=271), 118.0, 129.1, 129.8, 132.7, 135.3, 137.6, 141.1, 144.6, ˜155 (q, obscured due to baseline noise), 157.7, 186.4. 19F NMR −63.1. LC/MS 7.08 min, [M+1]+ 363.

Workup

customCrude product was chromatographed on silica gel with EtOAc/hexanes (10

Sources & evidence

ORD record: ord-8d45fb5756d24c118b3546f75de04736
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029397B2

Reaction notes

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