Sodium Carbonate → HCID 59272307, compound

HRID 1970279Notes

Reaction equation

HRID 1970279 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8](I)=[CH:9][CH:10]=3)[C:5]3([CH2:20][O:19][C:18]([NH2:21])=[N:17]3)[C:4]=2[CH:3]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24](B(O)O)[CH:23]=1.C(=O)([O-])[O-].[Na+].[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.COCCOC>[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:2]2[CH:15]=[CH:14][C:13]3[O:12][C:11]4[C:6](=[CH:7][C:8]([C:24]5[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=5)=[CH:9][CH:10]=4)[C:5]4([CH2:20][O:19][C:18]([NH2:21])=[N:17]4)[C:4]=3[CH:3]=2)[CH:23]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 58466329HCID 58466329, compound

Product 1

HCID 59272307HCID 59272307, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
95 °C

Procedure

Resealable tube was charged with 2′-bromo-7′-iodo-5H-spiro[oxazole-4,9′-xanthen]-2-amine (100 mg, 0.219 mmol), pyridin-3-ylboronic acid (81 mg, 0.656 mmol), Pd(PPh3)4 (50.6 mg, 0.044 mmol). DME (1 ml) and sodium carbonate (0.328 ml, 0.656 mmol) were added and the reaction mixture was capped with argon, sealed, and stirred at 95° C. for 16 hrs. The mixture was partitioned between DCM and water. The aqueous layer was removed and the organic layer was washed with brine, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (12 g column, 15-100% DCM/MeOH/NH4OH in DCM) to give material with impurity followed by second FC on silica (12 g column, 50-85% DCM/MeOH/NH4OH) to give 2′,7′-di(pyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine.

Workup

  1. customthe reaction mixture was capped with argon
  2. customsealed
  3. customThe mixture was partitioned between DCM and water
  4. customThe aqueous layer was removed
  5. washthe organic layer was washed with brine
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by flash chromatography on silica gel (12 g column, 15-100% DCM/MeOH/NH4OH in DCM)
  9. customto give material with impurity

Sources & evidence

ORD record
ord-f1bb620d6d65461d9f8566131b9cec00
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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