Potassium Carbonate → HCID 66919922, compound

HRID 1971731Notes

Reaction equation

HRID 1971731 reaction equation
[C:1]([N:5]1[C:29](=[O:30])[C:28]2[N:13]3[CH2:14][CH2:15][C:16]4[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:20][C:21]=4[C:12]3=[C:11](Br)[C:10]=2[CH2:9][O:8][CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>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.C(COC)OC>[C:1]([N:5]1[C:29](=[O:30])[C:28]2[N:13]3[CH2:14][CH2:15][C:16]4[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:20][C:21]=4[C:12]3=[C:11]([C:16]3[CH:15]=[CH:14][N:13]=[CH:12][CH:21]=3)[C:10]=2[CH2:9][O:8][CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 58124908HCID 58124908, compound

Product 1

HCID 66919922HCID 66919922, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 50 mg of 18d, 60 mg of K2CO3, 30 mg of 4-pyridylboronic acid-pinacolester and 15 mg of Pd(PPh3)4 in 2.5 ml of degassed 90% aq. dimethoxyethane was heated at 95° C. under N2 for 16 hr. The mixture was cooled and poured onto 1N NaOH and the product was extracted with ethyl acetate. The organic layer was washed twice with water, dried, concentrated and the residue was chromatographed on silica gel (using a gradient of heptane/acetone as eluent). The product was treated with ether, to give 25 mg of 18f as white crystals. Mp: 218-219° C. MS-ESI: [M+1] 490.17.

Workup

  1. temperatureThe mixture was cooled
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed twice with water
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was chromatographed on silica gel (
  7. additionThe product was treated with ether

Sources & evidence

ORD record
ord-74f4ad2c5a184d629131ad8d47b44b43
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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