2-Bromo-5-(2-(trimethylsilyl)ethynyl)pyridine → (3aRS,6aSR)-1-Methyl-3-(5-trimethylsilanylethynyl-pyridin-2-yl)-hexahydro-cyclopenta-imidazol-2-one

HRID 629229Notes

Reaction equation

HRID 629229 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][Si:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][N:3]=1.[CH3:14][N:15]1[CH:19]2[CH2:20][CH2:21][CH2:22][CH:18]2[NH:17][C:16]1=[O:23]>>[CH3:14][N:15]1[CH:19]2[CH2:20][CH2:21][CH2:22][CH:18]2[N:17]([C:2]2[CH:7]=[CH:6][C:5]([C:8]#[C:9][Si:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][N:3]=2)[C:16]1=[O:23]

Participants

3

Reactant 2

HCID 129830922-Bromo-5-(2-(trimethylsilyl)ethynyl)pyridineHCID 59655249(3aRS,6aSR)-1-Methyl-hexahydro-cyclopentaimidazol-2-one

Product 1

HCID 67436711(3aRS,6aSR)-1-Methyl-3-(5-trimethylsilanylethynyl-pyridin-2-yl)-hexahydro-cyclopenta-imidazol-2-one

Procedure

The title compound, an off-white solid, MS: m/e=314.1 (M+H+), was prepared in accordance with the general method of example 106, step 4 starting from 2-bromo-5-((trimethylsilyl)ethynyl)-pyridine (Example 37, step 1) and (3aRS,6aSR)-1-methylhexahydrocyclopenta[d]imidazol-2(1H)-one (Example 106, step 3).

Sources & evidence

ORD record
ord-257d7397e1b94a6bb4b812759ba8a84f
Source dataset
uspto-grants-2016_04
Patent number
US09315498B2

Reaction notes

Loading…