Sodium Carbonate → HCID 58485384, compound

HRID 1046268Notes

Reaction equation

HRID 1046268 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[CH2:7]([O:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14](Br)[N:13]=1)=[O:11])[CH3:8].[OH:19][C:20]([CH3:53])([CH3:52])[CH2:21][C@@:22]1([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[O:27][C:26](=[O:28])[N:25]([C@H:29]([C:31]2[CH:36]=[CH:35][C:34](B3OC(C)(C)C(C)(C)O3)=[CH:33][CH:32]=2)[CH3:30])[CH2:24][CH2:23]1>CN(C)C=O>[CH2:7]([O:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:34]2[CH:33]=[CH:32][C:31]([C@@H:29]([N:25]3[CH2:24][CH2:23][C@:22]([CH2:21][C:20]([OH:19])([CH3:52])[CH3:53])([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[O:27][C:26]3=[O:28])[CH3:30])=[CH:36][CH:35]=2)[N:13]=1)=[O:11])[CH3:8]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2758810Ethyl 6-BromopicolinateHCID 59532385(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one

Product 1

HCID 58485384HCID 58485384, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2 M aqueous Na2CO3 solution (1.46 mL) was added to a mixture of 6-bromo-pyridine-2-carboxylic acid ethyl ester (0.50 g) and (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-[(S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl]-1,3-oxazinan-2-one (0.70 g) in N,N-dimethyl-formamide (8 mL). The resulting mixture was sparged with argon for 10 min, before [1,1′-bis(diphenyl-phosphino)-ferrocene]dichloro-palladium(II) dichloromethane complex (72 mg) was added. The mixture was heated to 100° C. and stirred at this temperature overnight. After cooling to ambient temperature, water was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were dried (MgSO4) and the solvent was evaporated. The residue was purified by HPLC on reversed phase (methanol/water/NH4OH) to afford the title compound. Yield: 0.59 g (80% of theory); Mass spectrum (ESI+): m/z=503 [M+H]+.

Workup

  1. customThe resulting mixture was sparged with argon for 10 min, before [1,1′-bis(diphenyl-phosphino)-ferrocene]dichloro-palladium(II) dichloromethane complex (72 mg)
  2. additionwas added
  3. temperatureAfter cooling to ambient temperature
  4. additionwater was added
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. customthe solvent was evaporated
  8. customThe residue was purified by HPLC on reversed phase (methanol/water/NH4OH)

Sources & evidence

ORD record
ord-a9581da189b6486cba4314023ac54b14
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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