HCID 86623737, compound → HCID 11640042, compound

HRID 1173450Notes

Reaction equation

HRID 1173450 reaction equation
COC1C=CC(C[O:10][C:11]2[N:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]([CH2:33][C:34]([F:37])([F:36])[F:35])[C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([C:29]([F:32])([F:31])[F:30])[CH:22]=3)=[CH:13][CH:12]=2)=CC=1>[Pd]>[O:10]=[C:11]1[NH:16][CH:15]=[C:14]([O:17][CH2:18][CH2:19][N:20]([CH2:33][C:34]([F:37])([F:35])[F:36])[C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([C:29]([F:30])([F:31])[F:32])[CH:22]=2)[CH:13]=[CH:12]1

Participants

3

Reactant 1

HCID 86623737HCID 86623737, compound

Product 1

HCID 11640042HCID 11640042, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 4-[(2-{[6-({[4-(methyloxy)phenyl]methyl}oxy)-3-pyridinyl]oxy}ethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (0.270 g, 0.51 mmol; step C above) and Pd—C (0.027 g of 10 wt % on activated carbon (dry basis), ca. 50 wt % H2O, ca. 0.013 mmol Pd) was stirred under an atmosphere of H2 for 45 min and filtered through Celite. The filtrate was adsorbed onto a small amount of silica gel and purified by flash chromatography (MeOH/CH2Cl2), affording 0.160 g of the title compound as a colorless solid: MS (ESI) 406 (M+1).

Workup

  1. filtrationfiltered through Celite
  2. custompurified by flash chromatography (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-9c77961c51c440b3b435967f2f9149e9
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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