Ammonium Chloride → 6-Bromo-N*2*-(2-chloro-pyridin-4-yl)-pyridine-2,3-diamine

HRID 1524196Notes

Reaction equation

HRID 1524196 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([Cl:15])[CH:10]=2)[C:5]([N+:16]([O-])=O)=[CH:4][CH:3]=1.[Cl-].[NH4+]>CO.C1COCC1.[Zn]>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([Cl:15])[CH:10]=2)[C:5]([NH2:16])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 86651872(6-Bromo-3-nitro-pyridin-2-yl)-(2-chloro-pyridin-4-yl)-amine

Product 1

HCID 1317331266-Bromo-N*2*-(2-chloro-pyridin-4-yl)-pyridine-2,3-diamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

(6-Bromo-3-nitro-pyridin-2-yl)-(2-chloro-pyridin-4-yl)amine (step 1) (1 eq, 0.303 mmol, 100 mg) is dissolved in MeOH/THF (6 ml of a 1:1 mixture) and stirred for 5 minutes at RT. Zinc (22 eq, 6.6 mmol 350 mg) is added and the reaction mixture is stirred for a further 20 minutes. Saturated aqueous ammonium chloride (0.8 ml) is added to the reaction mixture and stirring continued at room temperature for 30 minutes. The mixture is filtered through CELITE® and the filtrate is diluted with water (10 ml) and extracted with EtOAc (2×10 ml). The organic portions are combined, dried (MgSO4) and concentrated in vacuo to afford the title compound; [M+H]+300.

Workup

  1. stirringthe reaction mixture is stirred for a further 20 minutes
  2. stirringstirring
  3. waitcontinued at room temperature for 30 minutes
  4. filtrationThe mixture is filtered through CELITE®
  5. additionthe filtrate is diluted with water (10 ml)
  6. extractionextracted with EtOAc (2×10 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-13cdae7466e3433bb064e912c7d1ce79
Source dataset
uspto-grants-2015_07
Patent number
US09079897B2

Reaction notes

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