Sodium borohydride → Methyl 5-amino-6-bromopyridin-2-ylcarbamate

HRID 2420875Notes

Reaction equation

HRID 2420875 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:12])[O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[N+:13]([O-])=O.[BH4-].[Na+]>CO.O.Cl[Ni]Cl>[NH2:13][C:3]1[CH:4]=[CH:5][C:6]([NH:8][C:9](=[O:12])[O:10][CH3:11])=[N:7][C:2]=1[Br:1]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 59166068Methyl 6-bromo-5-nitropyridin-2-ylcarbamate

Product 1

HCID 59165945Methyl 5-amino-6-bromopyridin-2-ylcarbamateYield 97.5%

Reagents, catalysts & solvents 3

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 6-bromo-5-nitropyridin-2-ylcarbamate (700 mg, 2.5 mmol) in CH3OH (20 mL) was added NiCl2 (1.2 g, 5.1 mmol) and NaBH4 (300 mg, 7.6 mmol) successively at 0° C. The mixture was stirred for 20 seconds. The reaction mixture was diluted with water and extracted with ethyl acetate (20 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum to give methyl 5-amino-6-bromopyridin-2-ylcarbamate (600 mg, 96%). 1H NMR (400 MHz, CDCl3) □ 7.75 (d, J=8.4 Hz, 1H), 7.13 (brs, 1H), 7.09 (d, J=8.8 Hz, 1H), 3.81 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate (20 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-56ff34877fd24699a15a7595a0b792b7
Source dataset
uspto-grants-2011_06
Patent number
US07956052B2

Reaction notes

Loading…