Nitrogen → HCID 22139450, compound

HRID 1825801Notes

Reaction equation

HRID 1825801 reaction equation
Cl[C:2]1[O:3][C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][C:6](=[O:8])[CH:7]=1.[CH:15]1[C:25]2[CH2:24][CH2:23][C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[S:20][C:19]=2[C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].N#N>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH:15]1[C:25]2[CH2:24][CH2:23][C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[S:20][C:19]=2[C:18]([C:2]2[O:3][C:4]([N:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[CH:5][C:6](=[O:8])[CH:7]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 66052622-Chloro-6-morpholinopyran-4-oneHCID 22139437HCID 22139437, compound

Product 1

HCID 22139450HCID 22139450, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

2-Chloro-6-morpholin-4-yl-pyran-4-one (3)(1.12 g, 5.2 mmol), 2-(10,11-Dihydro-dibenzo[b,f]thiepin-4-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (880 mg, 2.6 mmol), and ground potassium carbonate (720 mg, 5.2 mmol) were suspended in 1,4-dioxane (10 ml) and degassed for 5 minutes. bis(tri-t-butylphosphine)palladium (66 mg, 0.13 mmol) was then added and the reaction mixture was then heated at 90° C. for 4 hours under a vigorous stirring and a N2 atmosphere. The solvent was removed in vaccuo and the residue was then suspended in water (100 ml). The organics were extracted with dichloromethane (3×100 ml), combined, washed with saturated brine and dried over sodium sulphate. The solvent was removed in vaccuo and the residue was purified by column chromatography (silica; ethyl acetate:ethanol; 9:1) to give a pale brown solid (50 mg, 5%). 1HNMR (300 MHz, DMSO-d6): δH=3.24–3.32 (6H, m), 3.44 (2H, t), 3.66 (4H, t), 5.50 (1H, d), 6.10 (1H, d), 7.08–7.51 (7H, m); m/z (LC-MS, ESP), RT=4.48 min, (M++1)=392.

Workup

  1. customdegassed for 5 minutes
  2. customThe solvent was removed in vaccuo
  3. extractionThe organics were extracted with dichloromethane (3×100 ml)
  4. washwashed with saturated brine
  5. dry with materialdried over sodium sulphate
  6. customThe solvent was removed in vaccuo
  7. customthe residue was purified by column chromatography (silica; ethyl acetate:ethanol; 9:1)

Sources & evidence

ORD record
ord-845c542df9e24b62b4a4d46e971d15c6
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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