Water → 6-{[7-(Benzyloxy)quinolin-4-yl]oxy}-2-methyl-1-benzofuran-3-carboxylic acid

HRID 2076233Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:19])=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:20][C:21]1[CH:33]=[CH:32][C:24]2[C:25]([C:29]([OH:31])=[O:30])=[C:26]([CH3:28])[O:27][C:23]=2[CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CS(C)=O.CC(O)=O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:19])=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:20][C:21]3[CH:33]=[CH:32][C:24]4[C:25]([C:29]([OH:31])=[O:30])=[C:26]([CH3:28])[O:27][C:23]=4[CH:22]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

7-(benzyloxy)-4-chloroquinoline 90-B was prepared (see general synthesis Scheme I) from the commercially available compound 90-A (from Aldrich). A mixture of 90-B (2.8 g, 10.4 mmol), 6-hydroxy-2-methyl-1-benzofuran-3-carboxylic acid 90-C (2 g, 10.4 mmol) and Cs2CO3 (10.1 g, 31.4 mmol) in DMSO (70 ml) was heated to 130° C. for 2 hours. The solution was poured into water, neutralized with AcOH and extracted with EtOAc. The concentrated residue was purified by silica gel chromatography using 2-5% MeOH in CH2Cl2 to give 6-{[7-(benzyloxy)quinolin-4-yl]oxy}-2-methyl-1-benzofuran-3-carboxylic acid 90-D (4.2 g, 94% yield) as a solid.

Workup

extractionextracted with EtOAc
customThe concentrated residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-94948cd0a329472ea20b87a99fe48fd8
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923457B2

Reaction notes

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