Methanol → (2-Amino-6-methoxy-3-nitro-pyridin-4-yl)-benzyl-carbamic acid ethyl ester

HRID 639667Notes

Reaction equation

HRID 639667 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:26])[N:7]([C:15]1[CH:20]=[C:19](Br)[N:18]=[C:17]([NH2:22])[C:16]=1[N+:23]([O-:25])=[O:24])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:4].[CH3:27][OH:28]>C1COCC1>[CH2:3]([O:5][C:6](=[O:26])[N:7]([C:15]1[CH:20]=[C:19]([O:28][CH3:27])[N:18]=[C:17]([NH2:22])[C:16]=1[N+:23]([O-:25])=[O:24])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 86614485(2-Amino-6-bromo-3-nitro-pyridin-4-yl)-benzyl-carbamic acid ethyl ester

Product 1

HCID 67458821(2-Amino-6-methoxy-3-nitro-pyridin-4-yl)-benzyl-carbamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (9 mg) was dissolved carefully in methanol (0.5 ml) and this solution then added to a solution of (2-amino-6-bromo-3-nitro-pyridin-4-yl)-benzyl-carbamic acid ethyl ester (50 mg) in THF (0.5 ml) at room temperature. The reaction was stirred under nitrogen for 2 hours then the solution pre-absorbed directly onto silica gel. The mixture was purified by chromatography on an Isco Companion, eluting with ethyl acetate:heptane, increasing the gradient linearly from 20:80 to 60:40 over several column volumes. The desired fractions were combined and evaporated to provide the title compound (23 mg) as a yellow gum.

Workup

  1. customthe solution pre-absorbed directly onto silica gel
  2. customThe mixture was purified by chromatography on an Isco Companion
  3. washeluting with ethyl acetate
  4. temperatureheptane, increasing the gradient linearly from 20:80 to 60:40 over several column volumes
  5. customevaporated

Sources & evidence

ORD record
ord-62df5227314c4e1889d4168afcfbb177
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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