Sodium Carbonate → HCID 86667790, compound

HRID 509545Notes

Reaction equation

HRID 509545 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[Br:7][C:8]1[CH:9]=[C:10]([C:29]#[C:30][Si](C)(C)C)[C:11]([N:14]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N:12][CH:13]=1>CN(C=O)C.CCOC(C)=O.O>[Br:7][C:8]1[CH:9]=[C:10]([C:29]#[CH:30])[C:11]([N:14]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[N:12][CH:13]=1

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 67480069HCID 67480069, compound

Product 1

HCID 86667790HCID 86667790, compoundYield 100.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2M aqueous Na2CO3 (639.0 μL, 1.278 mmol) was added to a stirred solution of tert-butyl N-[5-bromo-3-(2-trimethylsilylethynyl)-2-pyridyl]-N-tert-butoxycarbonyl-carbamate (500 mg, 1.065 mmol) in DMF (1.5 mL) and the resulting suspension stirred at ambient temperature for 18 hours. The reaction mixture was diluted with EtOAc and water and the layers separated. The aqueous layer was extracted with EtOAc (×2) and the combined organic extracts washed with water (×3), brine (×2), dried (MgSO4), filtered and concentrated in vacuo to give the sub-title compound as an off-white solid (424 mg, 100% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.34 (s, 18H), 4.78 (s, 1H), 8.38 (d, J=2.4 Hz, 1H) and 8.66 (d, J=2.4 Hz, 1H) ppm; MS (ES+) 399.1.

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with EtOAc (×2)
  3. washthe combined organic extracts washed with water (×3), brine (×2)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6f0530d1ad7f43cba853cef90b18f08b
Source dataset
uspto-grants-2015_08
Patent number
US09096584B2

Reaction notes

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