Water → 3,4-difluoro-N-(2-methylpyrimidin-5-yl)benzamide

HRID 1271122Notes

Reaction equation

HRID 1271122 reaction equation
CB1OB(C)OB(C)O1.[C:10]([O-])([O-])=O.[Cs+].[Cs+].Cl[C:17]1[N:22]=[CH:21][C:20]([NH:23][C:24](=[O:33])[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[C:27]([F:32])[CH:26]=2)=[CH:19][N:18]=1.O>O1CCOCC1.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:32][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][C:28]=1[F:31])[C:24]([NH:23][C:20]1[CH:19]=[N:18][C:17]([CH3:10])=[N:22][CH:21]=1)=[O:33]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 574072TrimethylboroxineHCID 10149311Ica-069673

Product 1

HCID 101927903,4-difluoro-N-(2-methylpyrimidin-5-yl)benzamideYield 58.4%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of trimethylboroxine (27 μL, 0.19 mmol), Pd(dppf)2Cl2 (22 mg, 0.019 mmol), Cs2CO3 (185 mg, 0.57 mmol) and N-(2-chloro-pyrimidin-5-yl)-3,4-difluoro-benzamide (H) (50 mg, 0.19 numol) in dioxane (1 mL)/H2O (0.1 mL) was heated at 110–130° C. (bath temperature) for 1 h. The crude reaction mixture was filtered through a pad of celite and concentrated under reduced pressure. Purification of the crude material by column chromatography (hexanes/EtOAc) gave the desired product as white solid (27 mg, 57%).

Workup

  1. temperaturewas heated at 110–130° C. (bath temperature) for 1 h
  2. customThe crude reaction mixture
  3. filtrationwas filtered through a pad of celite
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the crude material by column chromatography (hexanes/EtOAc)

Sources & evidence

ORD record
ord-11e0d2f1c1f54b599ea2a3c7eceecdca
Source dataset
uspto-grants-2007_04
Patent number
US07205307B2

Reaction notes

Loading…