Sodium Carbonate → HCID 58102398, compound

HRID 406782Notes

Reaction equation

HRID 406782 reaction equation
C([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[CH:13]=[CH:12][N:11]([CH:14]2[CH2:16][CH2:15]2)[C:10](=[O:17])[CH:9]=1.[OH:18][C:19]([CH3:53])([CH3:52])[CH2:20][C@@:21]1([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[O:26][C:25](=[O:27])[N:24]([C@H:28]([C:30]2[CH:35]=[CH:34][C:33](B3OC(C)(C)C(C)(C)O3)=[CH:32][C:31]=2[CH3:45])[CH3:29])[CH2:23][CH2:22]1>CN(C)C=O>[CH:14]1([N:11]2[CH:12]=[CH:13][C:8]([C:33]3[CH:34]=[CH:35][C:30]([C@@H:28]([N:24]4[CH2:23][CH2:22][C@:21]([CH2:20][C:19]([OH:18])([CH3:53])[CH3:52])([C:46]5[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=5)[O:26][C:25]4=[O:27])[CH3:29])=[C:31]([CH3:45])[CH:32]=3)=[CH:9][C:10]2=[O:17])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 58102383HCID 58102383, compoundHCID 596356474-Bromo-1-cyclopropylpyridin-2(1H)-one

Product 1

HCID 58102398HCID 58102398, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2 M aqueous Na2CO3 solution (0.41 mL) was added to a mixture of 4-bromo-1-cyclopropyl-1H-pyridin-2-one (0.11 g) and (S)-6-(2-hydroxy-2-methyl-propyl)-3-{(S)-1-[2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-6-phenyl-[1,3]oxazinan-2-one (0.20 g) in N,N-dimethylformamide (2 mL). The resulting mixture was sparged with argon for 10 min prior to the addition of [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium(II) dichloromethane complex (33 mg). The mixture was heated to 100° C. and stirred at this temperature overnight. 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: 0.13 g (64% of theory); LC-MS (Method 5): tR=3.43 min; Mass spectrum (ESI+): m/z=501 [M+H]+.

Workup

  1. customThe resulting mixture was sparged with argon for 10 min
  2. additionto the addition of [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium(II) dichloromethane complex (33 mg)
  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-6bc3514c5273416686d80d77f3a02f69
Source dataset
uspto-grants-2014_06
Patent number
US08754076B2

Reaction notes

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