Sodium Carbonate → HCID 68759408, compound

HRID 2368047Notes

Reaction equation

HRID 2368047 reaction equation
C([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10](=[O:15])[CH:9]=1.[CH:16]1([CH:19]([C:38]2[CH:43]=[CH:42][C:41](B3OC(C)(C)C(C)(C)O3)=[CH:40][CH:39]=2)[N:20]2[CH2:25][CH2:24][C:23]([CH2:32][C:33]([OH:36])([CH3:35])[CH3:34])([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:22][C:21]2=[O:37])[CH2:18][CH2:17]1>CN(C)C=O>[CH:16]1([CH:19]([C:38]2[CH:43]=[CH:42][C:41]([C:8]3[CH:13]=[CH:12][N:11]([CH3:14])[C:10](=[O:15])[CH:9]=3)=[CH:40][CH:39]=2)[N:20]2[CH2:25][CH2:24][C:23]([CH2:32][C:33]([OH:36])([CH3:35])[CH3:34])([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:22][C:21]2=[O:37])[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 221323964-Bromo-1-methylpyridin-2(1H)-oneHCID 68758548HCID 68758548, compound

Product 1

HCID 68759408HCID 68759408, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2 M aqueous Na2CO3 solution (0.69 mL) was added to a mixture of 4-bromo-1-methyl-1H-pyridin-2-one (0.14 g) and 3-{cyclopropyl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]methyl}-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one (pure diastereomer; 0.35 g) in N,N-dimethylformamide (4 mL). The resulting mixture was sparged with argon for 10 min, before [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium(II) dichloromethane complex (57 mg) was added. The mixture was heated to 100° C. and stirred at this temperature for 4 h. After cooling the mixture to ambient temperature, water was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with water and brine and dried (MgSO4). The solvent was evaporated and the residue was purified by HPLC on reversed phase (methanol/water/NH4OH) to afford the title compound. Yield: 0.36 g (52% of theory); LC-MS (Method 1): tR=3.31 min; Mass spectrum (ESI+): m/z=487 [M+H]+.

Workup

  1. customThe resulting mixture was sparged with argon for 10 min, before [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium(II) dichloromethane complex (57 mg)
  2. additionwas added
  3. temperatureAfter cooling the mixture to ambient temperature
  4. additionwater was added
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washThe combined organic extracts were washed with water and brine
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated
  9. customthe residue was purified by HPLC on reversed phase (methanol/water/NH4OH)

Sources & evidence

ORD record
ord-e5c02a7fac7c47128a77920b44208a61
Source dataset
uspto-grants-2014_04
Patent number
US08703765B2

Reaction notes

Loading…