Sodium Carbonate → HCID 86729998, compound

HRID 2199775Notes

Reaction equation

HRID 2199775 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[N:10]=[N:11][N:12]([CH2:14][O:15][CH3:16])[CH:13]=2)=[N:6][CH:7]=1.[F:17][C:18]1[CH:19]=[C:20]([N:33]2[CH2:37][CH:36]([CH2:38][OH:39])[O:35][C:34]2=[O:40])[CH:21]=[CH:22][C:23]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Na+].[Na+]>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[F:17][C:18]1[CH:19]=[C:20]([N:33]2[CH2:37][CH:36]([CH2:38][OH:39])[O:35][C:34]2=[O:40])[CH:21]=[CH:22][C:23]=1[C:2]1[CH:7]=[N:6][C:5]([NH:8][C:9]2[N:10]=[N:11][N:12]([CH2:14][O:15][CH3:16])[CH:13]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 77177338HCID 77177338, compoundHCID 86729997HCID 86729997, compound

Product 1

HCID 86729998HCID 86729998, compoundYield 152.9%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

5-bromo-N-(1-(methoxymethyl)-1H-1,2,3-triazol-4-yl)pyridine-2-amine (0.318 g, 1.119 mmol), 3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-(hydroxylmethyl)oxazolidin-2-one (0.852 g, 2.527 mmol), sodium carbonate (0.357 g, 3.368 mmol), PdCl2(dppf)2 (0.064 g) were added into 20 mL dioxane and 2 drops of water, refluxed and reacted for 18 h under protection of nitrogen, cooled to room temperature, filtered, concentrated, chromatographed on a silica gel column (CH3OH:CH2Cl2=1:25), to obtain 0.709 g of crude 3-(3-fluoro-4-(6-((1-(methoxymethyl)-1H-1,2,3-triazol-4-yl)amino)pyridin-3-yl)phenyl)-5-(hydroxylmethyl)oxazolidin-2-one.

Workup

  1. temperaturerefluxed
  2. customreacted for 18 h under protection of nitrogen
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on a silica gel column (CH3OH:CH2Cl2=1:25)

Sources & evidence

ORD record
ord-fcf5eda620ff4c96bfe6c055f8f20aba
Source dataset
uspto-grants-2016_06
Patent number
US09359344B2

Reaction notes

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