Sodium Carbonate → HCID 86672403, compound

HRID 41166Notes

Reaction equation

HRID 41166 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:19]([O:21][CH3:22])=[O:20])[CH:5]=[C:6]2[C:11]=1[O:10][C:9]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[CH:8][C:7]2=[O:18].[C:23]([O:27][C:28]([N:30]1[CH:34]=[CH:33][CH:32]=[C:31]1B(O)O)=[O:29])([CH3:26])([CH3:25])[CH3:24].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:22][O:21][C:19]([C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([C:31]3[N:30]([C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:29])[CH:34]=[CH:33][CH:32]=3)[CH:3]=1)[O:10][C:9]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[CH:8][C:7]2=[O:18])=[O:20]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 58234996methyl 8-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylate

Product 1

HCID 86672403HCID 86672403, compoundYield 70.4%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred suspension of methyl 8-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylate (23 g, 62.47 mmol) in DME (300 mL) and water (30 mL) were added 1-(tert-butoxycarbonyl)-1H-pyrrol-2-ylboronic acid (14.50 g, 68.72 mmol), Na2CO3 (19.87 g, 187.41 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.877 g, 1.25 mmol). The mixture was degassed with argon and heated to 80° C. for 7 h. Reaction was cooled down and concentrated, the residue was dissolved in 300 mL of DCM and 300 mL of water. The organic phase was decanted, washed with brine then dried over MgSO4, filtered and concentrated to afford a crude compound which was purified on silica, eluting with 80% AcOEt in DCM. The solvents were evaporated to afford tert-butyl 2-(6-(methoxycarbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)-1H-pyrrole-1-carboxylate (20 g, 70%) as a white powder.

Workup

  1. customThe mixture was degassed with argon
  2. customReaction
  3. temperaturewas cooled down
  4. concentrationconcentrated
  5. dissolutionthe residue was dissolved in 300 mL of DCM
  6. customThe organic phase was decanted
  7. washwashed with brine
  8. dry with materialthen dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto afford a crude compound which
  12. customwas purified on silica
  13. washeluting with 80% AcOEt in DCM
  14. customThe solvents were evaporated

Sources & evidence

ORD record
ord-52afd7aa4d6940a3a6e433b0f25069de
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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