Sodium Carbonate → HCID 117700637, compound

HRID 873521Notes

Reaction equation

HRID 873521 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][C:4]=1[CH:12]1[C:25]2[C:24](=[O:26])[CH2:23][C:22]([CH3:28])([CH3:27])[CH2:21][C:20]=2[O:19][C:18]2[CH2:17][C:16]([CH3:30])([CH3:29])[CH2:15][C:14](=[O:31])[C:13]1=2.Cl[C:33]1[N:38]=[C:37]([C:39]#[N:40])[CH:36]=[CH:35][CH:34]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:33]2[N:38]=[C:37]([C:39]#[N:40])[CH:36]=[CH:35][CH:34]=2)=[CH:5][C:4]=1[CH:12]1[C:25]2[C:24](=[O:26])[CH2:23][C:22]([CH3:28])([CH3:27])[CH2:21][C:20]=2[O:19][C:18]2[CH2:17][C:16]([CH3:30])([CH3:29])[CH2:15][C:14](=[O:31])[C:13]1=2

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 1184246-Chloropyridine-2-carbonitrileHCID 131732562[4-Methoxy-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]boronic acid

Product 1

HCID 117700637HCID 117700637, compoundYield 95.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of the [4-methoxy-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]boronic acid produced in Example 1-1 (1.01 g, 2.37 mmol), 6-chloropyridine-2-carbonitrile (342 mg, 2.37 mmol), sodium carbonate (1.01 g, 9.48 mmol), and tetrakis(triphenylphosphine)palladium(0) (137 mg, 0.12 mmol) in 1,2-dimethoxyethane (20.1 ml) and water (8.7 ml) was prepared at room temperature, and the suspension thus prepared was then stirred at 90° C. for 45 minutes. After air-cooling, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. The organic layer thus obtained was dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the residue thus obtained was then purified by silica gel column chromatography (ethyl acetate:hexane=1:1, v/v). The solid thus obtained was washed with a mixed solution of diethyl ether and hexane, followed by collection by filtration and drying, to obtain the title compound (1.09 g, yield: 95%).

Workup

  1. customwas prepared at room temperature
  2. customthe suspension thus prepared
  3. temperatureAfter air-cooling
  4. extractionthe mixed solution was then extracted with ethyl acetate
  5. customThe organic layer thus obtained
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled away under reduced pressure
  8. customthe residue thus obtained
  9. customwas then purified by silica gel column chromatography (ethyl acetate
  10. customThe solid thus obtained
  11. washwas washed with a mixed solution of diethyl ether and hexane
  12. filtrationfollowed by collection by filtration
  13. customdrying

Sources & evidence

ORD record
ord-ff456e431acd4d7fa858dbf2fabcbee2
Source dataset
uspto-grants-2015_03
Patent number
US08975263B2

Reaction notes

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