Sodium Carbonate → HCID 59340069, compound

HRID 908560Notes

Reaction equation

HRID 908560 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](B3OC(C)(C)C(C)(C)O3)[CH:10]=2)[N:5]([CH3:21])[C:4](=[O:22])[C:3]=1[C:23]([NH:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:24].[Cl:32][C:33]1[CH:38]=[C:37](Cl)[N:36]=[CH:35][N:34]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.[Pd].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.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>[Cl:32][C:33]1[N:34]=[CH:35][N:36]=[C:37]([C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[N:5]([CH3:21])[C:4](=[O:22])[C:3]([C:23]([NH:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:24])=[C:2]3[OH:1])[CH:38]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 709434,6-DichloropyrimidineHCID 59340072HCID 59340072, compound

Product 1

HCID 59340069HCID 59340069, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a 10 ml reaction vial was charged ethyl 2-(4-hydroxy-1-methyl-2-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydroquinoline-3-carboxamido)acetate (200 mg, 465 μmol) in 1,4-dioxane (5 ml), 4,6-dichloropyrimidine (69 mg, 465 μmol), tetrakis(triphenylphosphine) palladium(0) (27 mg, 23 μmol) and sodium carbonate (0.7 ml, 1395 μmol), and the reaction vial was heated to 70° C. After reaction was complete, the reaction mixture was concentrated on a roto-evaporator, extracted with EtOAc, washed with water and brine (3× ea.) then dried with MgSO4 and concentrated on a roto-evaporator. The yellow solid was washed with EtOH and filtered and the solid was washed with ether. Yield=55 mg.

Workup

  1. customTo a 10 ml reaction
  2. customthe reaction
  3. customAfter reaction
  4. concentrationthe reaction mixture was concentrated on a roto-evaporator
  5. extractionextracted with EtOAc
  6. washwashed with water and brine (3× ea.)
  7. dry with materialthen dried with MgSO4
  8. concentrationconcentrated on a roto-evaporator
  9. washThe yellow solid was washed with EtOH
  10. filtrationfiltered
  11. washthe solid was washed with ether

Sources & evidence

ORD record
ord-18d68b92ec39448880179cae390b00aa
Source dataset
uspto-grants-2011_09
Patent number
US08017626B2

Reaction notes

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