Dimethylformamide → HCID 70980137, compound

HRID 1409353Notes

Reaction equation

HRID 1409353 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[N:6][CH:7]=1.CN(C=O)C.C([O-])([O-])=O.[Cs+].[Cs+].[N:26]1[CH:31]=[CH:30][CH:29]=[C:28](B(O)O)[CH:27]=1>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.[Fe+2].Cl[Cu]>[N:6]1[C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:4][CH:3]=[C:2]([C:28]2[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=2)[CH:7]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 27343783-Pyridinylboronic acidHCID 24997839tert-Butyl 5-bromopyridine-2-carboxylate

Product 1

HCID 70980137HCID 70980137, compound

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Into a solution of tert-butyl 5-bromopicolinate (3.5 g, 13.56 mmol) in DMF (40 ml) Pd(OAc)2 (0.152 g, 0.68 mmol), dppf (0.753 g, 1.37 mmol), CuCl (1.4 g, 13.57 mmol), Cs2CO3 (8.9 g, 27.13 mmol) and pyridin-3-yl boronic acid (3.4 g, 27.13 mmol) were added under inert atmosphere. The reaction mixture was stirred at 110° C. overnight and diluted with H2O. The mixture was filtered through a celite bed, and the filtrate was extracted with EtOAc. The organic layer was concentrated. Yield 1.75 g. 1H-NMR (400 MHz; CDCl3): δ 1.67 (s, 9H), 7.43-7.47 (m, 1H), 7.91 (d, J=8.0 Hz, 1H), 8.01 (dd, 1H), 8.17 (d, 1H), 8.70 (dd, 1H), 8.88 (d, 1H), 8.97 (d, 1H).

Workup

  1. filtrationThe mixture was filtered through a celite bed
  2. extractionthe filtrate was extracted with EtOAc
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-57f8814ff3ba4b43917c458d6a5fc8d2
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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