Sodium Carbonate → HCID 60037090, compound

HRID 966080Notes

Reaction equation

HRID 966080 reaction equation
[CH3:1][C:2]1([CH3:25])[O:7][C@@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:5]([NH:14][C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=2)=[O:16])[CH2:4][O:3]1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28](B(O)O)[CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(O)C.ClCCl.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][C:2]1([CH3:25])[O:7][C@@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:5]([NH:14][C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:28]3[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=3)=[CH:20][CH:19]=2)=[O:16])[CH2:4][O:3]1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 10456509HCID 10456509, compound

Product 1

HCID 60037090HCID 60037090, compoundYield 45.1%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 10 mg (0.0088 mmol) of tetrakis(triphenylphosphine)palladium(0) in ethylene glycol dimethyl ether (2.0 mL) was added 100 mg (0.22 mmol) of the product from Example 7. After stirring for 15 min, 27 mg (0.22 mmol) of pyridine-3-boronic acid dissolved in ethanol (0.20 mL) was added followed by 0.22 mL (0.44 mmol) of a 2 M sodium carbonate aqueous solution. The reaction mixture was heated to 80° C. for 12 h and then cooled to room temperature. The mixture was taken up in 10 mL of dichloromethane and washed with water. The organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. The product was purified by chromatography (hexanes/ethyl acetate) to yield 40 mg (45%) of the title compound.

Workup

  1. additionwas added
  2. temperaturecooled to room temperature
  3. washwashed with water
  4. dry with materialThe organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by chromatography (hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-67c21f7a4bd446f985b23544c79fbe6d
Source dataset
uspto-grants-2005_10
Patent number
US06951882B2

Reaction notes

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