1,10-Phenanthroline → HCID 58174131, compound

HRID 339797Notes

Reaction equation

HRID 339797 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][C:18]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][N:26]=4)[N:21]=[CH:20][N:19]=3)=[CH:11][CH:10]=2)[CH:3]=1.[F:28][C:29]([F:33])([F:32])[CH2:30][OH:31].C([O-])([O-])=O.[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>C(Cl)Cl.[Cu]I>[N:21]1[C:22]2[C:27](=[N:26][CH:25]=[CH:24][N:23]=2)[C:18]([NH:17][CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][C:4]3[CH:3]=[C:2]([O:31][CH2:30][C:29]([F:33])([F:32])[F:28])[CH:7]=[CH:6][N:5]=3)=[CH:10][CH:11]=2)=[N:19][CH:20]=1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 64092,2,2-TrifluoroethanolHCID 10796Cesium carbonateHCID 58174157HCID 58174157, compound

Product 1

HCID 58174131HCID 58174131, compoundYield 26.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-{4-[(4-iodopyridin-2-yl)oxy]phenyl}ethyl)pteridin-4-amine (300 mg, 0.64 mmol) and 2,2,2-trifluoroethanol (5 mL, 1.27 mmol) in a 45 mL Parr Bomb was added Cs2CO3 (412 mg, 1.27 mmol), 1,10-phenanthroline (22 mg, 0.127 mmol), and CuI (12 mg, 0.064 mmol). The reaction was held at 110° C. for 72 h, diluted with CH2Cl2, and washed with H2O. The organic layer was concentrated in vacuo and the residue was purified by preparative HPLC to afford pteridin-4-yl-(2-{4-[4-(2,2,2-trifluoroethoxy)-pyridin-2-yloxy]-phenyl}-ethyl)-amine (74 mg, 26%) as a yellow solid: mp 166° C.; EIMS m/z 442 ([M]+).

Workup

  1. washwashed with H2O
  2. concentrationThe organic layer was concentrated in vacuo
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-654baad086a44db88d92a7a9cd80ab28
Source dataset
uspto-grants-2014_11
Patent number
US08895568B2

Reaction notes

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