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

HRID 1477715Notes

Reaction equation

HRID 1477715 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]=[CH:41][C:40](Br)=[CH:39][C:38]=1[F:44])(=O)C>>[F:44][C:38]1[CH:39]=[C:40]([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:28])([F:30])[F:29])=[CH:25][CH:26]=4)[C:17](=[O:31])[N:16]=3)[CH2:11][CH:10]=2)[CH:41]=[CH:42][C:37]=1[OH:36]

Participants

3

Reactant 2

HCID 226485254-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 1178395164-[4-(3-Fluoro-4-hydroxyphenyl)-5,6-dihydropyridin-1(2H)-yl]-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-oneYield 41%

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 4-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 41%).

Workup

  1. customobtained by synthesis

Sources & evidence

ORD record
ord-32ac5190052f418e95c03b77d1c6eab0
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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