1,10-Phenanthroline → HCID 67471171, compound

HRID 2202150Notes

Reaction equation

HRID 2202150 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.Br[C:27]1[N:32]=[CH:31][CH:30]=[CH:29][N:28]=1.C([O-])([O-])=O.[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>C1(C)C=CC=CC=1.[Cu]I>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[N:10]([C:27]3[N:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 783452-BromopyrimidineHCID 7075709HCID 7075709, compound

Product 1

HCID 67471171HCID 67471171, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Procedure

A mixture of INTERMEDIATE 1 (3.0 g, 8.29 mol), 2-bromopyrimidine (2.9 g, 18.24 mol) and Cs2CO3 (10.8 g, 33.2 mol) in toluene (90 mL) in a pressure vessel was degassed with a stream of nitrogen. CuI (1.58 g, 8.29 mol) and 1,10-phenanthroline (2.99 g, 16.58 mol) were added. The mixture was degassed again with nitrogen, capped and heaed at 120° C. for 1.5 h. The mixture was allowed to cool to room temperature, filtered through a plug of Celite™, and washed with EtOAc. The EtOAc was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using gradient elution (10% to 50% ACN-DCM) to give the title compound as an off-white solid. LC-MS m/z 440.14 [M+H]+.

Workup

  1. customwas degassed with a stream of nitrogen
  2. customThe mixture was degassed again with nitrogen
  3. customcapped
  4. filtrationfiltered through a plug of Celite™
  5. washwashed with EtOAc
  6. customThe EtOAc was evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography
  8. washelution (10% to 50% ACN-DCM)

Sources & evidence

ORD record
ord-f9da44fa742c4860b88b7f2cf13b9ed5
Source dataset
uspto-grants-2016_06
Patent number
US09365539B2

Reaction notes

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