Sodium Dithionite → 5-bromo-N4-ethylpyridine-3,4-diamine

HRID 1394189Notes

Reaction equation

HRID 1394189 reaction equation
[Br:1][C:2]1[C:3]2[N:10](CC)[C:9]([C:13]3C(N)=NON=3)=[N:8][C:4]=2[CH:5]=[N:6][CH:7]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)C.O.ClCCl>[Br:1][C:2]1[C:3]([NH:10][CH2:9][CH3:13])=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 24489Sodium DithioniteHCID 443971924-(7-Bromo-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-1,2,5-oxadiazol-3-amine

Product 1

HCID 249037295-bromo-N4-ethylpyridine-3,4-diamine

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of the product of Step 1 (0.5 g, 2 mmol) in ethanol (8 ml)/water (10 ml) was stirred at 60° C. and sodium dithionite (2.12 g, 12.2 mmol) was added protionwise. After 10 minutes the mixture was cooled to room temperature, and diluted with water and dichloromethane. The organic phase was dried and evaporated in vacuo, the residue was used directly in the next reaction; 1H NMR (DMSO-d6) 7.76 (1H, s), 7.75 (1H, s), 5.0 (2H, br), 4.46 (1H, t, J=9.6 Hz), 3.26 (2H, m), 1.06 (3H, t, J=7.2 Hz).

Workup

  1. customThe organic phase was dried
  2. customevaporated in vacuo
  3. customthe residue was used directly in the next reaction

Sources & evidence

ORD record
ord-5702a78cb4e9455da3f029b1ab817159
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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