Potassium Carbonate → HCID 58124828, compound

HRID 1971730Notes

Reaction equation

HRID 1971730 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+].[N:38]1[CH:43]=[CH:42][CH:41]=[C:40](B(O)O)[CH:39]=1.[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(OCC)C.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:40]3[CH:39]=[N:38][CH:43]=[CH:42][CH:41]=3)[C:10]=2[CH2:9][O:8][CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 27343783-Pyridinylboronic acidHCID 58124908HCID 58124908, compound

Product 1

HCID 58124828HCID 58124828, compoundYield 56.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 50 mg of 18d, 60 mg of K2CO3, 20 mg of 3-pyridylboronic acid 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 reaction mixture was cooled and poured into 1N NaOH. The product was extracted with ethyl acetate. The organic extract was washed twice with water, dried, concentrated and the residue was chromatographed over silica gel, using a gradient of heptane/acetone as eluent. The product thus isolated was treated with diethyl ether, to provide 28 mg of 18e as white crystalline material. Mp 193-194° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe product was extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed twice with water
  5. customdried
  6. concentrationconcentrated
  7. customthe residue was chromatographed over silica gel
  8. customThe product thus isolated

Sources & evidence

ORD record
ord-a91ae84c9272454eaad7889e63a28f15
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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