Potassium Carbonate → HCID 59354768, compound

HRID 1776300Notes

Reaction equation

HRID 1776300 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10](=[O:15])[C:9]=2[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:29][C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=1>CN(C=O)C>[CH3:14][C:11]1([CH3:13])[C:10](=[O:15])[C:9]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:29][C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=3)=[CH:7][CH:6]=2)[O:12]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 135976068HCID 135976068, compound

Product 1

HCID 59354768HCID 59354768, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a room temperature solution of 5-(4-hydroxyphenyl)-2,2-dimethyl-4-(pyridin-4-yl)furan-3(2H)-one (280 mg, 0.9 mol) in DMF (5 mL), K2CO3 (413 mg, 2.98 mol) was added and the reaction mixture was stirred for 30 min. 2-Chloro methyl quinoline (235 mg, 1.09 mol) was then added to the reaction and stirring was continued for 2 h at 85° C. The reaction mixture was then quenched with cold water and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water, dried over Na2SO4 and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 2,2-dimethyl-4-(pyridin-4-yl)-5-(4-(quinolin-2-ylmethoxy)phenyl)furan-3(2H)-one (240 mg, 57%) as a solid. 1H NMR (509 MHz, d6-DMSO): δ 8.58-8.54 (m, 2 H), 8.42 (d, J=7.8 Hz, 1 H), 8.04-7.98 (m, 2 H), 7.80 (t, J=7.6 Hz, 1H), 7.68 (d, J=7.4 Hz, 1 H), 7.64 (t, J=7.6 Hz, 1 H), 7.58 (d, J=7.4 Hz, 2 H), 7.30-7.24 (m, 2 H), 7.19 (d, J=7.2 Hz, 2 H), 5.43 (s, 2 H), 1.50 (s, 6 H). MS: M+H; m/z=423.0. HPLC: 96%, (Condition-I).

Workup

  1. stirringstirring
  2. waitwas continued for 2 h at 85° C
  3. customThe reaction mixture was then quenched with cold water
  4. extractionextracted with EtOAc (2×50 mL)
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto obtain the crude product
  9. customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-e03a2774d1f146bd9e5206f205fc32eb
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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