2-(Chloromethyl)-5-(trifluoromethyl)thiophene → 4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1(2H)-yl]-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one

HRID 1477679Notes

Reaction equation

HRID 1477679 reaction equation
[CH3:1][C:2]1([CH3:22])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH2:14][CH2:13][N:12]([C:15]3[N:20]=[CH:19][N:18]=[C:17]([OH:21])[N:16]=3)[CH2:11][CH:10]=2)[O:3]1.Cl[CH2:24][C:25]1[S:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=1>>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:22])([CH3:1])[O:3][B:4]([C:9]2[CH2:14][CH2:13][N:12]([C:15]3[N:20]=[CH:19][N:18]([CH2:24][C:25]4[S:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=4)[C:17](=[O:21])[N:16]=3)[CH2:11][CH:10]=2)[O:5]1

Participants

3

Reactant 2

HCID 545735382-(Chloromethyl)-5-(trifluoromethyl)thiopheneHCID 178431090HCID 178431090, compound

Product 1

HCID 1236159664-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1(2H)-yl]-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-oneYield 46%

Procedure

4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1(2H)-yl]-1,3,5-triazin-2-ol (3.32 g, 10.9 mmol) synthesized in Reference Synthesis Example 345 and 2-(chloromethyl)-5-(trifluoromethyl)thiophene were used to obtain the title compound (2.36 g, yield 46%) by synthesis in a similar manner to Reference Synthesis Example 16.

Sources & evidence

ORD record
ord-503eb16c272b474bbe7f1d045b5f67cf
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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