3-(Trifluoromethyl)phenol → 4-Dimethylamino-2-(3-thienylmethyloxy)-6-(meta-trifluoromethylphenoxy)pyridine

HRID 55135Notes

Reaction equation

HRID 55135 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].Cl[C:15]1[CH:20]=[C:19]([N:21]([CH3:23])[CH3:22])[CH:18]=[C:17]([O:24][CH2:25][C:26]2[CH:30]=[CH:29][S:28][CH:27]=2)[N:16]=1>CN(C)C(=O)C.[Cu]I>[CH3:22][N:21]([CH3:23])[C:19]1[CH:20]=[C:15]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=2)[N:16]=[C:17]([O:24][CH2:25][C:26]2[CH:30]=[CH:29][S:28][CH:27]=2)[CH:18]=1

Participants

6

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydrideHCID 199574072-Chloro-4-dimethylamino-6-(3-thienylmethyloxy)pyridine

Product 1

HCID 199574004-Dimethylamino-2-(3-thienylmethyloxy)-6-(meta-trifluoromethylphenoxy)pyridine

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 31374DimethylacetamideSolvent2×

Procedure

To a solution of meta-trifluoromethylphenol (1.27 g, 0.0020×4.0 mol) in 20 ml of dry N,N-dimethylacetamide, sodium hydride (0.313 g, (ca.60% in mineral oil), 0.0020×4.0 mol) was added. After the bubbling ceased, a solution of 2-chloro-4-dimethylamino-6-(3-thienylmethyloxy)pyridine (0.526 g, 0.0020 mol) in 20 ml of dry N,N-dimethylacetamide was added dropwise, then CuI (0.186 g, 0.0020×0.5 mol) was added thereto and the resultant solution was stirred for 24 hours at the temperature of 170° to 180° C.

Sources & evidence

ORD record
ord-9d8ce96f1e2f4bf88603a54003fce961
Source dataset
uspto-grants-1997_04
Patent number
US05624942

Reaction notes

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