Sodium Carbonate → HCID 59272388, compound

HRID 1970276Notes

Reaction equation

HRID 1970276 reaction equation
[Br:1][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]=[C:26](B(O)O)[CH:25]=[N:24][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>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([C:26]4[CH:27]=[N:22][CH:23]=[N:24][CH:25]=4)=[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

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 58466329HCID 58466329, compound

Product 1

HCID 59272388HCID 59272388, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
65 °C

Procedure

50 ml Flask was charged with 2′-bromo-7′-iodo-5H-spiro[oxazole-4,9′-xanthen]-2-amine (1.000 g, 2.188 mmol), pyrimidin-5-ylboronic acid (0.380 g, 3.06 mmol), tetrakis(triphenylphosphine)palladium (0.126 g, 0.109 mmol) and DME (10 mL). Sodium carbonate (3.28 mL, 6.56 mmol) was added and the reaction mixture was stirred at 65° C. for 16 hrs. The brown mixture with precipitate was filtered and the solids were washed with DME (3 ml), water (5 ml) and methanol (5 ml), dried on air. The material was treated with 10 ml of DCM and filtered, filtrate was evaporated to afford to afford 2′-bromo-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine as white solid

Workup

  1. filtrationThe brown mixture with precipitate was filtered
  2. washthe solids were washed with DME (3 ml), water (5 ml) and methanol (5 ml)
  3. customdried on air
  4. additionThe material was treated with 10 ml of DCM
  5. filtrationfiltered
  6. customfiltrate was evaporated
  7. customto afford

Sources & evidence

ORD record
ord-65dd80aa5b264957876c7494dcd86515
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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