Cesium carbonate → HCID 71542432, compound

HRID 2199768Notes

Reaction equation

HRID 2199768 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[N:10]=[N:11][N:12]([CH3:14])[N:13]=2)=[N:6][CH:7]=1.[F:15][C:16]1[CH:17]=[C:18]([N:31]2[CH2:35][C@H:34]([CH2:36][OH:37])[O:33][C:32]2=[O:38])[CH:19]=[CH:20][C:21]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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]>[F:15][C:16]1[CH:17]=[C:18]([N:31]2[CH2:35][C@H:34]([CH2:36][OH:37])[O:33][C:32]2=[O:38])[CH:19]=[CH:20][C:21]=1[C:2]1[CH:7]=[N:6][C:5]([NH:8][C:9]2[N:10]=[N:11][N:12]([CH3:14])[N:13]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 66678633HCID 66678633, compoundHCID 86729992HCID 86729992, compound

Product 1

HCID 71542432HCID 71542432, compoundYield 30%

Reagents, catalysts & solvents 3

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

Procedure

5-bromo-N-(2-methyl-2H-tetrazol-5-yl)pyridine-2-amine (200 mg, 0.78 mmol), (R)-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-(hydroxylmethyl)oxazolidin-2-one (317 mg, 0.94 mmol), cesium carbonate (508 mg, 1.56 mmol) and Pd(dppf)Cl2 (90 mg, 0.16 mmol) were dissolved in 16 mL dioxane and 4 mL water, heated to 100° C. and reacted for 6 h. The solvent was evaporated to dryness, and the solid was separated by a silica gel column (dichloromethane:methanol=40:1) to obtain (R)-3-(3-fluoro-4-(6-((2-methyl-2H-tetrazol-5-yl)amino)pyridin-3-yl)phenyl)-5-(hydroxylmethyl)oxazolidin-2-one 90 mg, at a yield of 30%.

Workup

  1. customreacted for 6 h
  2. customThe solvent was evaporated to dryness
  3. customthe solid was separated by a silica gel column (dichloromethane:methanol=40:1)

Sources & evidence

ORD record
ord-7e2c4e012764456babb0277cc106e545
Source dataset
uspto-grants-2016_06
Patent number
US09359344B2

Reaction notes

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