4-(Boc-amino)pyridine → 4-[N-(tert-butoxycarbonyl)amino]-1-[2-(3-methoxy-4-nitrophenyl)-2-oxoethyl]pyridinium bromide

HRID 1987842Notes

Reaction equation

HRID 1987842 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([O:14][CH3:15])[CH:6]=1)=[O:4].[C:16]([O:20][C:21]([NH:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>C(#N)C.CC(C)=O>[Br-:1].[C:16]([O:20][C:21]([NH:23][C:24]1[CH:25]=[CH:26][N+:27]([CH2:2][C:3]([C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([O:14][CH3:15])[CH:6]=2)=[O:4])=[CH:28][CH:29]=1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 2

HCID 99902104-(Boc-amino)pyridineHCID 179579432-Bromo-1-(3-methoxy-4-nitrophenyl)-1-ethanone

Product 1

HCID 866075524-[N-(tert-butoxycarbonyl)amino]-1-[2-(3-methoxy-4-nitrophenyl)-2-oxoethyl]pyridinium bromideYield 93%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent

Procedure

2.90 g (10.6 mmol) of 2-bromo-1-(3-methoxy-4-nitrophenyl)-1-ethanone [described in Bull. Soc. Chim. Fr., (1962), pp 2255-2261] are added in portions to 2.07 g (10.6 mmol) of 4-[N-(tert-butoxycarbonyl)amino]pyridine [described in Tetrahedron; (2001), vol 57(43), pp 9033-9044] in suspension in 10 mL of acetonitrile and 20 mL of acetone. The reaction medium becomes homogeneous by stirring at room temperature and then precipitation occurs. The medium is stirred for 1 hour at room temperature. The precipitate formed is filtered, washed with acetone and dried. 4.6 g of a white powder are obtained.

Workup

  1. customprecipitation
  2. stirringThe medium is stirred for 1 hour at room temperature
  3. customThe precipitate formed
  4. filtrationis filtered
  5. washwashed with acetone
  6. customdried

Sources & evidence

ORD record
ord-4ea8730d60ab43e588a14f5fdf2925df
Source dataset
uspto-grants-2009_06
Patent number
US07553845B2

Reaction notes

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