Potassium Carbonate → HCID 66815652, compound

HRID 2367926Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 6-(3′-hydroxyphenyl)-pyridine-2-carboxylate (7) (250 mg, 1.1 mmol, 1.0 eq.) and 2-(6′-bromohexyloxy)tetrahydropyran (420 mg, 0.36 mL, 1.6 mmol, 1.5 eq.) in DMF (3 mL) was added K2CO3 (460 mg, 3.3 mmol, 3.0 eq.). The mixture was stirred vigorously overnight at 70° C. and then concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with NaH2PO4 buffer (pH 5, 1M) and brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography on silica using ethyl acetate:hexanes to provide 300 mg (65%) of 12. TLC Rf=0.5 (ethyl acetate:hexanes 1:1), MS m/z 330 (fragment after elimination of the THP group) [M+H]+

Workup

concentrationconcentrated in vacuo
dissolutionThe residue was dissolved in ethyl acetate
washwashed with NaH2PO4 buffer (pH 5, 1M) and brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe crude product was purified by flash chromatography on silica

Sources & evidence

ORD record: ord-86a76cce3e1b438c802cb1a27b5f082a
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703700B2

Reaction notes

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