Nitrogen → HCID 22139416, compound

HRID 1825798Notes

Reaction equation

HRID 1825798 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.CC1(C)C(C)(C)OB([C:23]2[C:33]3[S:32][C:31]4[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=4[CH2:29][C:28](=[O:38])[C:27]=3[CH:26]=[CH:25][CH:24]=2)O1.C(=O)([O-])[O-].[K+].[K+].N#N>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:9]1([C:4]2[O:3][C:2]([C:23]3[C:33]4[S:32][C:31]5[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=5[CH2:29][C:28](=[O:38])[C:27]=4[CH:26]=[CH:25][CH:24]=3)=[CH:7][C:6](=[O:8])[CH:5]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

7

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 66052622-Chloro-6-morpholinopyran-4-oneHCID 22139442HCID 22139442, compound

Product 1

HCID 22139416HCID 22139416, compoundYield 29.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

2-Chloro-6-morpholin-4-yl-pyran-4-one (3)(215 mg, 1 mmol), 6-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-11H-dibenzo[b,f]thiepin-10-one (352 mg, 1 mmol), and ground potassium carbonate (276 mg, 2 mmol) were suspended in 1,4-dioxane (10 ml) and degassed for 5 minutes. Pd(PPh3)4 (57 mg, 0.05 mmol) was then added and the reaction mixture was then heated at 90° C. for 4hours 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 the title compound as a pale brown solid (0.12 g, 29%). 1HNMR (300 MHz, DMSO-d6): δH=3.40 (4H, t), 3.70 (4H, t), 4.43 (2H, s), 5.55 (1H, d), 6.29 (1H, d), 7.25–7.55 (5H, m), 7.78–7.81 (1H, m), 8.20–8.22 (1H, m); m/z (LC-MS, ESP), RT=4.12 min, (M++1)=406.

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-0e50c51d5213469586da5e72fd8cc5c4
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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