1,10-Phenanthroline → HCID 57949388, compound

HRID 2427704Notes

Reaction equation

HRID 2427704 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:7](=[O:15])[N:6]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1)[CH2:5]2.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.CC(C)([O-])C.[Na+]>N1C=CC=CC=1.CCCCCC.C1CC=CCCC=C1.C1CC=CCCC=C1.[Ni].C(OCC)(=O)C>[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([C:2]2[CH:3]=[C:4]3[C:8](=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=2)[C:7](=[O:15])[N:6]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2)[CH2:5]3)[CH2:31][CH2:30]1

Participants

9

Reactant 4

HCID 13181,10-PhenanthrolineHCID 531671-MethylpiperazineHCID 23676156Sodium t-butoxideHCID 866299795-Bromo-2-(4-trifluoromethoxy-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one

Product 1

HCID 57949388HCID 57949388, compoundYield 31.3%

Reagents, catalysts & solvents 4

HCID 6433264Bis(1,5-cyclooctadiene)nickelCatalystHCID 1049PyridineSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-bromo-2-(4-trifluoromethoxy-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.110 g, 0.25 mmol), 1-methyl piperazine (0.037 mL, 0.33 mmol), Ni(COD)2 (0.013 g, 0.004 mmol), 1,10-phenanthroline (0.005 g, 0.025 mmol), and sodium tertiary-butoxide (0.034 g, 0.35 mmol) in pyridine (2 mL) was heated to reflux for 3 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 5-(4-methyl-piperazin-1-yl)-2-(4-trifluoromethoxy-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.037 g, 31%). 1H NMR (300 MHz, CDCl3/CD3OD): δ (ppm) 2.26 (s, 3H), 2.52 (m, 2H), 2.80 (m, 4H), 3.40 (m, 2H), 4.36 (s, 2H), 4.76 (s, 2H), 7.20-7.52 (m, 6H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h

Sources & evidence

ORD record
ord-6802c8a0eca24f22a5d6b1eaf1b30f82
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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