Sodium Carbonate → HCID 86672436, compound

HRID 41216Notes

Reaction equation

HRID 41216 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:20]([O:22][CH3:23])=[O:21])[CH:5]=[C:6]2[C:11]=1[O:10][C:9]([N:12]1[CH2:17][CH2:16][O:15][C@H:14]([CH3:18])[CH2:13]1)=[CH:8][C:7]2=[O:19].[C:24]([O:28][C:29]([N:31]1[CH:35]=[CH:34][CH:33]=[C:32]1B(O)O)=[O:30])([CH3:27])([CH3:26])[CH3:25].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:23][O:22][C:20]([C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([C:32]3[N:31]([C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:30])[CH:35]=[CH:34][CH:33]=3)[CH:3]=1)[O:10][C:9]([N:12]1[CH2:17][CH2:16][O:15][C@H:14]([CH3:18])[CH2:13]1)=[CH:8][C:7]2=[O:19])=[O:21]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 58235000(R)-methyl 8-bromo-2-(2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylate

Product 1

HCID 86672436HCID 86672436, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Bis(triphenylphosphine) palladium(II) chloride (0.448 g, 0.63 mmol) was added in one portion to a stirred slurry of (R)-methyl 8-bromo-2-(2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylate (10.06 g, 25 mmol), 1-(tert-butoxycarbonyl)-1H-pyrrol-2-ylboronic acid (6.46 g, 30.00 mmol) and sodium carbonate (7.95 g, 75.00 mmol) in DME (140 mL) and water (28 mL). The mixture was degassed with argon for 15 mins then heated at 80° C. for 6 h. The solvent was evaporated, water was added to the residue and the mixture was extracted with DCM. The combined organic phases were washed with water, brine, dried over MgSO4 and concentrated to give crude (R)-tert-butyl 2-(6-(methoxycarbonyl)-2-(2-methylmorpholino)-4-oxo-4H-chromen-8-yl)-1H-pyrrole-1-carboxylate containing ˜20% of starting material (13.98 g). Mass Spectrum: m/z [M+H]+=469.

Workup

  1. customThe mixture was degassed with argon for 15 mins
  2. customThe solvent was evaporated
  3. additionwater was added to the residue
  4. extractionthe mixture was extracted with DCM
  5. washThe combined organic phases were washed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3dc35aa3ac4c42dda72a581966baa61f
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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