Sodium hydride → HCID 178455462, compound

HRID 1774742Notes

Reaction equation

HRID 1774742 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:14])([CH3:13])[C@@H:8]1[CH2:12][CH2:11][CH2:10][NH:9]1)([CH3:4])([CH3:3])[CH3:2].[Br:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([CH2:22]Cl)[CH:21]=1.[H-].[Na+]>>[Br:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([CH2:22][N:9]2[CH2:10][CH2:11][CH2:12][C@H:8]2[C:7]([CH3:14])([CH3:13])[O:6][SiH2:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH:21]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 117012593-Bromo-5-(chloromethyl)pyridineHCID 131734725HCID 131734725, compound

Product 1

HCID 178455462HCID 178455462, compound

Procedure

In analogy to the procedure described for the preparation of intermediates A-12 [B], (S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidine (intermediate A-3 [A]) was reacted with 3-bromo-5-chloromethyl-pyridine (intermediate A-12 [A]) in presence of NaH to give the title compound as a yellow solid. MS: 385.2, 387.2 (M+H+).

Sources & evidence

ORD record
ord-5502f46194734d0ca4dbfeb332535e6a
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

Loading…