Sodium Carbonate → 6-(2-morpholinoethoxy)-3-phenyl-2-(pyridin-3-yl)-1H-inden-1-one

HRID 331265Notes

Reaction equation

HRID 331265 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:18]=[C:17]3[C:13]([C:14]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[C:15](Br)[C:16]3=[O:19])=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[Na+].[Na+].O1[CH2:38][CH2:37]OCC1.O>CCOC(C)=O.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>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:18]=[C:17]3[C:13]([C:14]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[C:15]([C:2]4[CH:3]=[N:4][CH:5]=[CH:37][CH:38]=4)[C:16]3=[O:19])=[CH:12][CH:11]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 218864351,4-Dioxane--water (1/1)HCID 703076206-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-one

Product 1

HCID 509405096-(2-morpholinoethoxy)-3-phenyl-2-(pyridin-3-yl)-1H-inden-1-oneYield 64%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a microwave reaction vial, 6-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-one (1.0 g, 2.5 mmol) obtained in Step 6,3-pyridinylboronic acid (470 mg, 3.8 mmol, 1.5 eq), Pd(PPh3)4 (180 mg, 6 mol %), Na2CO3 (800 mg, 3.0 eq), and dioxane/H2O (4:1, 5 mL) were sequentially charged. The reaction vial was placed into a microwave reactor and irradiated at 150° C. for 20 min. After cooling to room temperature, the reaction was diluted with EtOAc and dried over MgSO4. The mixture was filtered through a Celite pad while rinsing with EtOAc and then concentrated in vacuo. The residue was purified by prep HPLC (CH3CN/H2O=1:1) to afford the desired product (640 mg, 64%).

Workup

  1. customTo a microwave reaction vial
  2. customThe reaction
  3. customvial was placed into a microwave reactor
  4. customirradiated at 150° C. for 20 min
  5. dry with materialdried over MgSO4
  6. filtrationThe mixture was filtered through a Celite pad
  7. washwhile rinsing with EtOAc
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by prep HPLC (CH3CN/H2O=1:1)

Sources & evidence

ORD record
ord-aec82f5adf9c4751a89d1ce8dd286435
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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