Oxygen → HCID 22281804, compound

HRID 636550Notes

Reaction equation

HRID 636550 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:3]=1[CH2:4][N:5]1[CH:10]=[C:9](Br)[C:8](=[O:12])[N:7]2[C:13]([CH3:27])=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH:24]4[CH2:26][CH2:25]4)=[CH:18][CH:17]=3)[N:15]=[C:6]12.O=O.[C:35]1(B(O)O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C([O-])([O-])=O.[K+].[K+]>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.COCCOC>[F:1][C:2]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:3]=1[CH2:4][N:5]1[CH:10]=[C:9]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:8](=[O:12])[N:7]2[C:13]([CH3:27])=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH:24]4[CH2:26][CH2:25]4)=[CH:18][CH:17]=3)[N:15]=[C:6]12

Participants

7

Reactant 4

HCID 977OxygenHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 22281800HCID 22281800, compound

Product 1

HCID 22281804HCID 22281804, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

The compound obtained in Example 24 (0.02 g, 0.04 mmol) is added to DME (30 ml), which is oxygen free. To this mixture is added phenylboronic acid (0.0054 g, 0.044 mmol), 2N aqueous K2CO3 solution (0.1 ml), tetrakis(triphenylphosphine)palladium(0) (0.0046 g, 0.004 mmol). Then the mixture is refluxed for 3 hours under argon atmosphere. The residual reaction mixture is partitioned between ethyl acetate (100 ml) and water (30 ml). The aqueous layer is extracted with ethyl acetate (30 ml). The combined organic extract is dried over Na2SO4 and concentrated under reduced pressure to give the residue, which is chromatographed on silica gel to afford white crystals (0.016 g, 78%).

Workup

  1. temperatureThen the mixture is refluxed for 3 hours under argon atmosphere
  2. customThe residual reaction mixture
  3. customis partitioned between ethyl acetate (100 ml) and water (30 ml)
  4. extractionThe aqueous layer is extracted with ethyl acetate (30 ml)
  5. extractionThe combined organic extract
  6. dry with materialis dried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto give the residue, which
  9. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-cd3e53bc1d8642a89cd795f67c7d71a6
Source dataset
uspto-grants-2001_02
Patent number
US06194419B1

Reaction notes

Loading…