Potassium Carbonate → HCID 66857786, compound

HRID 1191320Notes

Reaction equation

HRID 1191320 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:7](=[O:21])[C:6]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)=[C:5]2[OH:27].C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][CH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.[OH-].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1)[C:7](=[O:21])[C:6]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)=[C:5]2[O:27][CH2:35][CH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 27732864-(Bromomethyl)oxaneHCID 66856287HCID 66856287, compound

Product 1

HCID 66857786HCID 66857786, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-4-hydroxy-1-(4-methoxybenzyl)-3-(thiophen-2-yl)quinolin-2(1H)-one (1.2 g, 2.8 mmol) in tetrahydrofuran (0.3 M, 10 mL) at room temp was added potassium carbonate (1.2 g, 8.4 mmol). 4-bromomethyl tetrahydropyran (1.0 g, 5.6 mmol) was added to this solution mixture. The reaction mixture was left stirring overnight. The crude reaction mixture was poured into 1 N sodium hydroxide (100 mL). The product was extracted with ethyl acetate (3×50 mL). The combined organic extractions were dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified via flash chromatography (silica, 7:3 hexanes/ethyl acetate) to yield 6-bromo-4-(tetrahydro-2H-pyran-4-ylmethoxy)-1-(4-methoxybenzyl)-3-(thiophen-2-yl)quinolin-2(1H)-one as an orange oil. LCMS (M+H)=539.8.

Workup

  1. waitThe reaction mixture was left
  2. customThe crude reaction mixture
  3. extractionThe product was extracted with ethyl acetate (3×50 mL)
  4. extractionThe combined organic extractions
  5. dry with materialwere dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified via flash chromatography (silica, 7:3 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-2b6241fad0db4d87984b9762fdfafc61
Source dataset
uspto-grants-2014_03
Patent number
US08680116B2

Reaction notes

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