[(1E)-3-[(tert-butyldimethylsilyl)oxy]buta-1,3-dien-1-yl]dimethylamine → 3-(Tert-butyldimethylsilyloxy)-6-(3-chloropyridin-2-yl)-n,n-dimethyl-6-(trifluoromethyl)cyclohex-2-enamine

HRID 2197597Notes

Reaction equation

HRID 2197597 reaction equation
[Cl:1][C:2]1[C:3]([C:8]([C:10]([F:13])([F:12])[F:11])=[CH2:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[Si:14]([O:21][C:22](=[CH2:28])/[CH:23]=[CH:24]/[N:25]([CH3:27])[CH3:26])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C1(C)C=CC=CC=1>[Si:14]([O:21][C:22]1[CH2:28][CH2:9][C:8]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=2)([C:10]([F:11])([F:13])[F:12])[CH:24]([N:25]([CH3:27])[CH3:26])[CH:23]=1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 6060661[(1E)-3-[(tert-butyldimethylsilyl)oxy]buta-1,3-dien-1-yl]dimethylamineHCID 67499168Pyridine, 3-chloro-2-[1-(trifluoromethyl)ethenyl]-

Product 1

HCID 674998243-(Tert-butyldimethylsilyloxy)-6-(3-chloropyridin-2-yl)-n,n-dimethyl-6-(trifluoromethyl)cyclohex-2-enamineYield 61.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of Example 26A (612 mg, 2.95 mmol) and (E)-3-(tert-butyldimethylsilyloxy)-N,N-dimethylbuta-1,3-dien-1-amine (966 mg, 4.25 mmol) in toluene (2.5 mL) was heated on a microwave at 60° C. for 30 minutes, and then 70° C. for 30 minutes. Purified by silica gel chromatography (AnaLogix® SF25-40G; 50 micron silica; elution with 0-50% ethyl acetate in hexane at 30 mL/min) to provide the title compound (787 mg, 1.81 mmol, 61.4% yield) as a light yellow oil. MS (DCI/NH3) m/e 435 (M+H)+.

Workup

  1. customPurified by silica gel chromatography (AnaLogix® SF25-40G; 50 micron silica; elution with 0-50% ethyl acetate in hexane at 30 mL/min)

Sources & evidence

ORD record
ord-c8c9852f2bd84555aaffee19a597ae81
Source dataset
uspto-grants-2012_12
Patent number
US08338603B2

Reaction notes

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