((4-Bromo-2-fluorobenzyl)oxy)(tert-butyl)dimethylsilane → [({2-[(1-{5-[3-Fluoro-4-(hydroxymethyl)phenyl]pyridin-2-yl}piperidin-4-yl)methyl]-5-hydroxy-6-methylpyrimidin-4-yl}carbonyl)amino]acetic acid

HRID 1626832Notes

Reaction equation

C([O:3][C:4](=[O:38])[CH2:5][NH:6][C:7]([C:9]1[C:14]([O:15]CC2C=CC=CC=2)=[C:13]([CH3:23])[N:12]=[C:11]([CH2:24][CH:25]2[CH2:30][CH2:29][N:28]([C:31]3[CH:36]=[CH:35][C:34](Br)=[CH:33][N:32]=3)[CH2:27][CH2:26]2)[N:10]=1)=[O:8])C.Br[C:40]1[CH:54]=[CH:53][C:43]([CH2:44][O:45][Si](C(C)(C)C)(C)C)=[C:42]([F:55])[CH:41]=1>>[F:55][C:42]1[CH:41]=[C:40]([C:34]2[CH:35]=[CH:36][C:31]([N:28]3[CH2:27][CH2:26][CH:25]([CH2:24][C:11]4[N:10]=[C:9]([C:7]([NH:6][CH2:5][C:4]([OH:3])=[O:38])=[O:8])[C:14]([OH:15])=[C:13]([CH3:23])[N:12]=4)[CH2:30][CH2:29]3)=[N:32][CH:33]=2)[CH:54]=[CH:53][C:43]=1[CH2:44][OH:45]

Participants

Reactant 2

HCID 57685175((4-Bromo-2-fluorobenzyl)oxy)(tert-butyl)dimethylsilane

HCID 123856667Ethyl({[5-(benzyloxy)-2-{[1-(5-bromopyridin-2-yl)piperidin-4-yl]methyl}-6-methylpyrimidin-4-yl]carbonyl}amino)acetate

Product 1

HCID 52932571[({2-[(1-{5-[3-Fluoro-4-(hydroxymethyl)phenyl]pyridin-2-yl}piperidin-4-yl)methyl]-5-hydroxy-6-methylpyrimidin-4-yl}carbonyl)amino]acetic acidYield 21%

Procedure

In accordance with Examples 19-(2), 1-(10), 22-(4) and 1-(13), but using ethyl({[5-(benzyloxy)-2-{[1-(5-bromopyridin-2-yl)piperidin-4-yl]methyl}-6-methylpyrimidin-4-yl]carbonyl}amino)acetate instead of tert-butyl 5-(benzyloxy)-2-{[1-(5-bromopyridin-2-yl)piperidin-4-yl]methyl}-6-methylpyrimidine-4-carboxylate, and [(4-bromo-2-fluorobenzyl)oxy](tert-butyl)dimethylsilane instead of tert-butyl[(4-iodobenzyl)oxy]dimethylsilane, the title compound (yield 21%) was afforded as a white solid.

Sources & evidence

ORD record: ord-fd5b5224b90a4ae2ae2c2d2783d9a001
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785462B2

Reaction notes

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