p-Toluenesulfonic acid → rac-7-(2-chlorophenyl)-6-(4-chlorophenyl)-2-(3-fluorophenyl)-2H-pyrano[2,3-b]pyridin-4(3H)-one

HRID 1673221Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)=[CH:10][CH:11]([C:15](=[O:26])[CH2:16][CH:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)[OH:18])[C:12](=O)[N:13]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[O:18][CH:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)[CH2:16][C:15](=[O:26])[C:11]2=[CH:10][C:9]=1[C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 120 °C

Procedure

The product of step A (200 mg, 0.42 mmol) was dissolved in toluene (2 mL) and p-toluenesulfonic acid (30 mg, 0.16 mmol) was added. The reaction was heated at 120° C. for 4 h and allowed to cool overnight. The reaction was diluted with EtOAc and washed with a saturated solution of NaHCO3, brine, dried (Na2SO4), filtered and concentrated The residue was purified by flash chromatography on silica gel gradient eluted with 0-30% EtOAc in hexane to afford the title compound. (LC-2) HPLC/MS: 464.2 (M+1), 466.2 (M+3); Rt=2.61 min.

Workup

temperatureto cool overnight
washwashed with a saturated solution of NaHCO3, brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated The residue
customwas purified by flash chromatography on silica gel gradient
washeluted with 0-30% EtOAc in hexane

Sources & evidence

ORD record: ord-5d8e5119a5504984876cbb0a8b2da5d3
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07999107B2

Reaction notes

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