Potassium Carbonate → 2-(4-Methoxymethoxy-thianthren-1-yl)-6-morpholin-4-yl-pyran-4-one

HRID 33797Notes

Reaction equation

HRID 33797 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:18]2[S:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[S:10][C:9]=2[C:8](B2OC(C)(C)C(C)(C)O2)=[CH:7][CH:6]=1.Cl[C:29]1[O:30][C:31]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[CH:32][C:33](=[O:35])[CH:34]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:18]2[S:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[S:10][C:9]=2[C:8]([C:29]2[O:30][C:31]([N:36]3[CH2:37][CH2:38][O:39][CH2:40][CH2:41]3)=[CH:32][C:33](=[O:35])[CH:34]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66052622-Chloro-6-morpholinopyran-4-oneHCID 59797447HCID 59797447, compound

Product 1

HCID 597974342-(4-Methoxymethoxy-thianthren-1-yl)-6-morpholin-4-yl-pyran-4-oneYield 101.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

2-(4-Methoxymethoxy-thianthren-1-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (6.23 g, 17.14 mmol), 2-chloro-6-morpholin-4-yl-pyran-4-one (3) (6.99 g, 17.40 mmol) and powdered potassium carbonate (7.20 g, 52.20 mmol) were suspended in anhydrous dioxane (60 ml) under a nitrogen atmosphere. The mixture was degassed for 15 minutes before the addition of tetrakis(triphenylphosphino)palladium (1.2 g, 5% eq) and then degassed for a further 15 minutes after addition. The reaction was then heated at 90° C. for 24 hours. Water (60 ml) was added and the mixture extracted with EtOAc (3×30 ml). The organic extracts were then dried using MgSO4, filtered and concentrated in vacuo to yield a dark yellow oil. The crude residue was then purified by flash chromatography (SiO2) (9:1—EtOAc/MeOH) to give the title compound (7.93 g, 79%) as a green powder. m/z (LC-MS, ESP): RT=4.39 min, (M++1)=456

Workup

  1. customThe mixture was degassed for 15 minutes before the addition of tetrakis(triphenylphosphino)palladium (1.2 g, 5% eq)
  2. customdegassed for a further 15 minutes
  3. additionafter addition
  4. additionWater (60 ml) was added
  5. extractionthe mixture extracted with EtOAc (3×30 ml)
  6. customThe organic extracts were then dried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto yield a dark yellow oil
  10. customThe crude residue was then purified by flash chromatography (SiO2) (9:1—EtOAc/MeOH)

Sources & evidence

ORD record
ord-fb6de198a3b84fbe8e2a6d9321b16117
Source dataset
uspto-grants-2008_09
Patent number
US07429660B2

Reaction notes

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