5-Bromo-2-fluorophenyl acetate → 4-[4-(4-Fluoro-3-hydroxyphenyl)-5,6-dihydropyridin-1(2H)-yl]-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one

HRID 1477716Notes

Reaction equation

HRID 1477716 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH2:14][CH2:13][N:12]([C:15]3[N:20]=[CH:19][N:18]([CH2:21][C:22]4[S:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=4)[C:17](=[O:31])[N:16]=3)[CH2:11][CH:10]=2)O1.C([O:36][C:37]1[CH:42]=[C:41](Br)[CH:40]=[CH:39][C:38]=1[F:44])(=O)C>>[F:44][C:38]1[CH:39]=[CH:40][C:41]([C:9]2[CH2:14][CH2:13][N:12]([C:15]3[N:20]=[CH:19][N:18]([CH2:21][C:22]4[S:23][C:24]([C:27]([F:29])([F:30])[F:28])=[CH:25][CH:26]=4)[C:17](=[O:31])[N:16]=3)[CH2:11][CH:10]=2)=[CH:42][C:37]=1[OH:36]

Participants

3

Reactant 2

HCID 910399425-Bromo-2-fluorophenyl acetateHCID 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)-one

Product 1

HCID 1178393184-[4-(4-Fluoro-3-hydroxyphenyl)-5,6-dihydropyridin-1(2H)-yl]-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-oneYield 35%

Procedure

The synthesis was performed using a crude product obtained by synthesis using 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1(2H)-yl]-1-{[5-(t rifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one synthesized in Reference Synthesis Example 346 and 5-bromo-2-fluorophenyl acetate in a similar manner to Reference Synthesis Example 139, in a similar manner to Reference Synthesis Example 2 (two step yield 35%).

Workup

  1. customobtained by synthesis

Sources & evidence

ORD record
ord-279ecc581ae74045b8af7dd356ce19a6
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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