Water → tert-Butyl 3-(2-(6-bromopyridin-2-yl)-2-methylhydrazono)-9-azabicyclo[3.3.1]nonane-9-carboxylate

HRID 469693Notes

Reaction equation

HRID 469693 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8][N:9]=[C:10]2[CH2:17][CH:16]3[N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:12]([CH2:13][CH2:14][CH2:15]3)[CH2:11]2)[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:28]I.O>CN(C=O)C>[Br:1][C:2]1[N:7]=[C:6]([N:8]([CH3:28])[N:9]=[C:10]2[CH2:17][CH:16]3[N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:12]([CH2:13][CH2:14][CH2:15]3)[CH2:11]2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58092251tert-Butyl 3-(2-(6-bromopyridin-2-yl)hydrazono)-9-azabicyclo[3.3.1]nonane-9-carboxylate

Product 1

HCID 58092250tert-Butyl 3-(2-(6-bromopyridin-2-yl)-2-methylhydrazono)-9-azabicyclo[3.3.1]nonane-9-carboxylateYield 103.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 3-(2-(6-bromopyridin-2-yl)hydrazono)-9-azabicyclo[3.3.1]nonane-9-carboxylate (609 mg, 1.49 mmol) was dissolved in DMF, and NaH (60%, 65 mg, 1.63 mmol) was added. After 30 min, MeI (232 mg, 1.63 mmol, 102 μL) was added, and stirring continued for 30 min. The mixture was poured into water and extracted with ethyl acetate. The ethyl acetate was concentrated to provide the crude product (655 mg, >100%) as a red oil: ESI MS m/z 423 [M+H]+.

Workup

  1. waitcontinued for 30 min
  2. extractionextracted with ethyl acetate
  3. concentrationThe ethyl acetate was concentrated

Sources & evidence

ORD record
ord-3622cd6862f3434d8e81cc35fb47d27a
Source dataset
uspto-grants-2014_01
Patent number
US08629158B2

Reaction notes

Loading…