4-trimethylsilylaniline → 4-(3-(trifluoromethyl)pyridin-2-yl)-N-(4-(trimethylsilyl)phenyl)benzamide

HRID 404560Notes

Reaction equation

HRID 404560 reaction equation
[CH3:1][Si:2]([CH3:11])([CH3:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[F:12][C:13]([F:30])([F:29])[C:14]1[C:15]([C:20]2[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=2)=[N:16][CH:17]=[CH:18][CH:19]=1>>[F:30][C:13]([F:12])([F:29])[C:14]1[C:15]([C:20]2[CH:28]=[CH:27][C:23]([C:24]([NH:7][C:6]3[CH:8]=[CH:9][C:3]([Si:2]([CH3:11])([CH3:10])[CH3:1])=[CH:4][CH:5]=3)=[O:25])=[CH:22][CH:21]=2)=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 100349574-trimethylsilylaniline2×HCID 534262354-(3-(Trifluoromethyl)pyridin-2-YL)benzoic acid2×

Product 1

HCID 513492014-(3-(trifluoromethyl)pyridin-2-yl)-N-(4-(trimethylsilyl)phenyl)benzamideYield 68.3%

Procedure

Compound A-04 can be synthesized according to method 2. Just R1 and R3 of Scheme 2 are, respectively, CF3 and p-SiMe3. namely: compound 6 is 4-trimethylsilyl aniline (compound 6a 35 mg); compound 10 is 4-(3-trifluoromethylpyridine-2-yl)benzoic acid (compound 10b); compound 12 is compound A-04 (60 mg, yield 68.3%).

Workup

  1. customCompound A-04 can be synthesized

Sources & evidence

ORD record
ord-b901d51c217b443f8e604afc263a5c7c
Source dataset
uspto-grants-2014_06
Patent number
US08748610B2

Reaction notes

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