Triphenylphosphine → N-[6-(1-bromoethyl)pyridin-2-yl]-2,2-dimethylpropanamide

HRID 1042336Notes

Reaction equation

O[CH:2]([C:4]1[N:9]=[C:8]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[CH:7]=[CH:6][CH:5]=1)[CH3:3].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Br:36]N1C(=O)CCC1=O>C(Cl)Cl>[Br:36][CH:2]([C:4]1[N:9]=[C:8]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[CH:7]=[CH:6][CH:5]=1)[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of N-[6-(1-hydroxyethyl)pyridin-2-yl]-2,2-dimethylpropanamide (1 g, 4.49 mmol, 1 eq.) in 20 ml of DCM was cooled to 0° C. and PPh3 (1.65 g, 6.29 mmol, 1.4 eq.) was added followed by N-Bromosuccinimide (0.96 g, 5.39 mmol, 1.2 eq.). The reaction was stirred at 0° C. for 1 h and at r.t. for 1 h. The solvent was removed and residue purified by chromatography on silica gel to give N-[6-(1-bromoethyl)pyridin-2-yl]-2,2-dimethylpropanamide (1.025 g, 79% yield) as a clear oil.

Workup

customThe solvent was removed
customresidue purified by chromatography on silica gel

Sources & evidence

ORD record: ord-a8c5328354224b56bbcc755a5641efdb
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557849B2

Reaction notes

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